New learning discoveries about 4488-22-6

4488-22-6, The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4488-22-6,[1,1′-Binaphthalene]-2,2′-diamine,as a common compound, the synthetic route is as follows.

To a mixture of BINAM (852 mg, 3.0 mmol) and HOAc (1.8 Ml, 30mmol) was added acetic anhydride (312 muL, 3.3 mmol), and the solution was stirred at room temperature overnight. NaOH was added until pH > 7 to quench the reaction, and the solution was extracted with DCM (15 mL¡Á 3). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel using hexane-EtOAc as the eluent, to give A-1; yield: 880 mg (89%).

4488-22-6, The synthetic route of 4488-22-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhang, Yu; Mao, Mao; Ji, Yi-Gang; Zhu, Jie; Wu, Lei; Tetrahedron Letters; vol. 57; 3; (2016); p. 329 – 332;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

Brief introduction of 602-09-5

With the synthetic route has been constantly updated, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol,belong chiral-catalyst compound

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO41,mainly used in chemical industry, its synthesis route is as follows.,602-09-5

7H-Dibenzo[c,g]carbazole (12c): 30 g (0.105 mol) of 1,1′-binaphthalene-2,2′-diol (BINOL), 30 g (0.224 mol) of (NH4)2SO3¡¤H2O and 90 ml of 26 % NH4OH was heated at 200C in a 160 ml autoclave (Parr Instrument) for 5 days (after 48 h the pressure dropped from 45 to 18 bar). Upon cooling down, the crude matter was washed with boiling water, dissolved in a 1:1 mixture of EtOH:HCl (conc.), extracted with hot toluene (3×200 ml) and concentrated under vacuum. Residual starting material was removed by extraction with 2M NaOH solution (3×200 ml). Organic layers were combined, dried over Na2SO4, filtered, concentrated and chromatographed on a SiO2 column (50 % DCM in hexanes). Yield: 7.7 g (27 %) of dark-yellow crystalline solid. M.p. 154-156C. 1H NMR (CDCl3, 300 MHz): delta 9.22 (d, J=8.5, 2H), 8.79 (br, s, 1H), 8.05 (dd, J=8.1, 1.3, 2H), 7.89 (d, J=8.7, 2H), 7.74-7.65 (m, 4H), 7.53 (ddd, J=8.0, 6.9, 1.0, 2H).

With the synthetic route has been constantly updated, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol,belong chiral-catalyst compound

Reference£º
Article; Kerner, Luka?; Gmucova, Katarina; Ko?i?ek, Jozef; Pet?i?ek, Vaclav; Putala, Martin; Tetrahedron; vol. 72; 44; (2016); p. 7081 – 7092;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

Downstream synthetic route of (S)-(1-Ethylpyrrolidin-2-yl)methanamine

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine,belong chiral-catalyst compound

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO264,mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20¡ã C. was added N-phenyl glycinonitrile (0.264 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cycloheptylamine (0.25 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at rt. Then, S-(-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography eluding with 96:3:1 methylene chloride:methanol:conc. ammonium hydroxide to yield 143, (0.300 g, 33percent) mp 53-55¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 6.9 min, 94.1percent purity; MS (ESI): m/z 449 (M+H, 100), 381 (1.2), 353 (16.2), 226 (19.9), 225 (54.3), 212 (20.5), 177 (18.3), 164 (9.6).

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine,belong chiral-catalyst compound

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishma Reddy, Velagala Venkata Rama Murali; Sesila Sridevi, Bhatlapenumarthy; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209882; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

Share a compound : 250285-32-6

250285-32-6 is used more and more widely, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, cas is 250285-32-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,250285-32-6

IPr-HCI (82.04 mg, 0.193 mmol), [Pd(cin)(M-CI)]2 (50.0 mg, 0.096 mmol), a magnetic stir bar and acetone (0.8 mL) were charged into a vial . The mixture was stirred at 60 C for 1 h . The solvent was removed and the product was dried under vacuum . The product was obtained as a dark orange powder in a 99% ( 132 mg) yield . Single crystals were grown by vapour diffusion of hex- ane into a solution of the complex in DCM . XH IMMR (400 MHz, CDCh) : delta (ppm) = 9.19 (s, 1 H), 8.32 (d, J = 1.60 Hz, 2H), 7.56-7.52 (m, 2H), 7.46 (d, J = 7.44 Hz, 2H), 7.33 (d, J = 7.75 Hz, 4H), 7.21 (m, 3H), 5.66 (s, 1 H), 4.46 (s, 1 H), 3.83 (s, 1 H), 2.90 (s, 1 H), 2.48- 2.41 (m, 4H), 1.27 (d, J = 6.81 Hz, 12H), 1.19 (d, J = 6.76 Hz, 12H) . 13C {XH } NMR (100 MHz, CDCh): delta (ppm) = delta 144.9 (C), 136.7 (CH), 131.8 (C), 129.7 (C), 128.4 (CH), 127.7 (CH), 127.5 (CH), 124.5 (CH), 105.0 (C), 28.8 (CHs), 24.4 (CHs), 23.7 (CHs) . Elemental analysis: Expected : C 63.02, H 7.05 N 4.08 Found : C 62.92 H 7.14 N 4.15

250285-32-6 is used more and more widely, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Reference£º
Patent; UMICORE AG & CO. KG; NOLAN, Steven P.; (47 pag.)WO2018/115029; (2018); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

Some tips on 1121-22-8

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

It is a common heterocyclic compound, the chiral-catalyst compound, trans-Cyclohexane-1,2-diamine, cas is 1121-22-8 its synthesis route is as follows.,1121-22-8

General procedure: Aryl halide (1.0 equiv) and aliphatic diamines/amino alcohol (2.0 equiv) were taken in a 100 ml round bottom flask along with 100-150 mg of the chitosan copper catalyst in CH3CN (15 ml) solvent. The resultant mixture was heated at reflux for 3-6 h. After completion of the reaction (the complete consumption of starting materials was confirmed by TLC) the reaction mixture was extracted with ethylacetate. The separated organic phase was concentrated to get the gummy liquid product 3. The chitosan copper catalyst was collected by simple decanting off the reaction mixture. The recovered catalyst was then washed thoroughly with ethyl acetate 2-3 times,dried under vacuum at 50C and used for another run.

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Reference£º
Article; Bodhak, Chandan; Kundu, Ashis; Pramanik, Animesh; Tetrahedron Letters; vol. 56; 2; (2015); p. 419 – 424;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

Downstream synthetic route of 173035-10-4

The synthetic route of 173035-10-4 has been constantly updated, and we look forward to future research findings.

173035-10-4, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Pd(OAc)2 (0.110 g, 0.50 mmol) and SIMes.HCl (0.170 g, 0.50 mmol) were dissolved in THF (15 mL). The resulting mixture was heated to 55 C along with magnetic stirring for 2 h. After cooling down the mixture to RT, it was purified on silica-gel column. The resulting orange solution was transferred to the Schlenk tube and the solvent was removed under vacuum. The oily residue was dissolved in CH2Cl2 (5 mL) and water (3-10 mL) was added to remove unreacted SIMes.HCl. Organic phase was separated and hexane (5 mL) was slowly added. After 24 h the product was filtered off and dried in vacuum. Yield: 50%. Crystals suitable for X-ray analysis were obtained by slow evaporation of the CH2Cl2/hexane solution. 1H NMR (500 MHz; CDCl3;TMS): delta=6.92 (s, 8H, ArH), 6.77 (s, 8H, NCH2-NCH2), 2.47 (s, 12H, p-ArCH3), 1.94 (s, 24H, oArCH3) 13C NMR (125 MHz; CDCl3; TMS): delta=170.9 (s, N2C), 137.5 (s, NC), 136.1 (s, o-CCH3), 135.7 (s, p-CCH3), 128.8 (s, CH), 122.4 (s, CH2), 21.25 (s, o-CH3), 18.9 (s, p-CH3) elemental analysis calcd (%) C42H52Cl4N4Pd2: C 52.14, H 5.42, N 5.79; found: C 51.15, H 5.09, N 5.30., 173035-10-4

The synthetic route of 173035-10-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Gorna, Marta; Szulmanowicz, Micha? S.; Gniewek, Andrzej; Tylus, W?odzimierz; Trzeciak, Anna M.; Journal of Organometallic Chemistry; vol. 785; (2015); p. 92 – 99;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

The important role of 4488-22-6

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

Name is [1,1′-Binaphthalene]-2,2′-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 17-iodo-5alpha-androsta-16-ene 1 (0.5 mmol), 2,2′-diamino-1,1′-binaphthalene 2 (varied from 1.0 mmol to 0.125 mmol) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon (filled with argon) at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 C and analysed by TLC. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (3 20 mL), 5% hydrochloric acid (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL). The organic phase was dried over Na2SO4, filtered and evaporated to give a solid material. All compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200 mm), EtOAc/CHCl3 or hexane/CHCl3 (the exact ratios are specified in Section 4.4 for each compound). 4.3. Characterisation of the products (Fig. 3) (Sax)-3: Yield: 410 mg (72%). Off-white yellow solid, mp 137-142 C; [Found: C, 84.55; H, 7.65; N, 4.70; C40H44N2O requires C,84.46; H, 7.80; N, 4.93]; Rf (5% EtOAc/CHCl3) 0.68. 1H NMR (CDCl3) delta: 8.94 (1H, d, 9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.94 (1H, d,8.2 Hz, H-50), 7.87 (1H, d, 8.5 Hz, H-300), 7.82 (1H, d, 7.5 Hz, H-400), 7.43 (1H, dt, 6.3 Hz, 1.6 Hz, H-60), 7.35 (1H, s, NH), 7.31 (1H, dt,8.5 Hz, 0.8 Hz, H-70), 7.29-7.26 (2H, m, H-600 , H-600), 7.23 (1H, dt,6.8 Hz, 1.1 Hz, H-700), 7.16 (1H, d, 8.7 Hz, H-80), 6.96 (1H, d, 8.2 Hz,H-800), 6.21 (1H, dd, 2.9 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.7 Hz, 6.5 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd,16.7 Hz, 11.9 Hz, 1.4 Hz, 15-CHaHb), 1.07-0.54 (23H, m, skeleton protons), 0.78 (3H, s, 19-CH3), 0.62 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.6, 150.4, 143.0, 140.0, 135.7, 133.8, 132.5. 131.1, 130.3, 129.3, 128.3, 128.2, 128.1, 127.5, 126.8, 125.3, 124.9, 123.6, 122.8, 120.4, 119.7, 118.1, 110.5, 56.8, 54.7, 47.2, 45.3, 38.4, 36.3, 34.2, 33.7, 31.8, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 16.0, 12.1. IR (KBr, m(cm1)): 3440 (amide-NH), 3398 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (relint.): 551.4 (29), 285.2 (100). [alpha]D20 = 37.1 (c 1.34, CHCl3). (Rax)-3: Yield: 114 mg (20%). Off-white solid substance; [Found:C, 84.30; H, 7.66; N, 4.77; C40H44N2O requires C, 84.46; H, 7.80; N,4.93]; Rf (5% EtOAc/CHCl3) 0.72. 1H NMR (CDCl3) delta: 8.95 (1H, d,9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.93 (1H, d, 7.9 Hz, H-50), 7.87 (1H, d, 8.9 Hz, H-300), 7.82 (1H, d, 7.8 Hz, H-400), 7.43 (1H, dt,6.4 Hz, 1.2 Hz, H-60), 7.36 (1H, s, NH), 7.31 (1H, dt, 8.6 Hz, 0.8 Hz,H-70), 7.29-7.26 (2H, m, H-6”, H”), 7.23 (1H, dt, 6.9 Hz, 1.5 Hz,H-7”), 7.16 (1H, d, 8.5 Hz, H-8′), 6.96 (1H, d, 8.4 Hz, H-8”), 6.21 (1H, dd, 3.1 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.3 Hz, 6.4 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd, 16.6 Hz,11.7 Hz, 2.0 Hz, 15-CHaHb), 1.07-0.53 (23H, m, skeleton protons), 0.77 (3H, s, 19-CH3), 0.31 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.5, 150.4, 143.1, 140.2, 135.7, 133.8, 132.4, 131.1, 130.3, 129.3, 128.4, 128.3, 128.2, 127.5, 126.8, 125.3, 124.9, 123.6,122.8, 120.4, 119.7, 118.0, 110.6, 56.8, 54.8, 47.2, 45.2, 38.4, 36.3, 34.2, 33.7, 31.7, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 15.5, 12.1. IR(KBr, m (cm1)): 3441 (amide-NH), 3396 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (rel int.): 551.4 (29), 285.2 (100). [alpha]D20 = +191.5 (c 0.914, CHCl3). (Sax)-4: Yield: 102 mg (12%). Beige solid substance; [Found: C,84.31; H, 8.35; N, 3.12; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.69. 1H NMR (CDCl3) alpha: 8.94 (2H, d,9.2 Hz, H-3′), 8.08 (2H, d, 9.2 Hz, H-4′), 7.95 (2H, d, 8.2 Hz, H-5′),7.46 (2H, dt, 7.2 Hz, 0.9 Hz, H-6′), 7.35 (2H, dt, 7.2 Hz, 0.9 Hz, H-7′), 7.1 (2H, d, 9.3 Hz, H-8′), 7.13 (2H, s, NH), 6.05 (2H, dd, 3.1 Hz, 1.5 Hz, H-16), 2.02 (2H, ddd, 16.8 Hz, 6.4 Hz, 3.1 Hz, 15-CHaHb), 1.88 (2H, dd, 9.9 Hz, 3.1 Hz, 14-CH), 1.75 (2H, ddd, 16.8 Hz,11.7 Hz, 1.5 Hz, 15-CHaHb), 1.69-0.54 (44H, m, skeleton protons), 0.77 (6H, s, 19-CH3), 0.57 (6H, s, 18-CH3). 13C NMR (CDCl3) alpha: 163.6, 150.2, 140.0, 136.0, 135.2, 132.4, 131.3, 130.0, 128.2,127.5, 125.3, 124.9, 120.5, 118.1, 56.6, 54.8, 47.2, 45.4, 38.4, 36.3, 34.2, 33.6, 31.7, 31.4, 29.0, 28.8, 26.8, 22.1, 20.5, 16.1, 12.1. IR (KBr, m (cm1)): 3408 (amide-NH), 1677 (CON), 1621 (CC). MS m/z (rel int.): 853.6 ((M+H)+); 875.6 ((M+Na)+), 891.5 ((M+K)+). [alpha]D20 = +12.0 (c 0.418, CHCl3). (Rax)-4: Yield: 85 mg (10%). Beige solid substance; [Found: C,84.28; H, 8.30; N, 3.06; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.74. 1H NMR (CDCl3) alpha: 8.95 (2H, d,9.0 Hz, H-3′), 8.08 (2H, d, 9.0 Hz, H-4′), 7.96 (2H, d, 7.8 Hz, H-5′), 7.46 (2H, dt, 7.8 Hz, 0.9 Hz, H-6’…

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

Reference£º
Article; Mikle, Gbor; Boros, Borbla; Kollr, Lszl; Tetrahedron Asymmetry; vol. 25; 23; (2014); p. 1527 – 1531;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

Some tips on Benzo-18-crown 6-Ether

With the complex challenges of chemical substances, we look forward to future research findings about 14098-24-9,belong chiral-catalyst compound

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is Benzo-18-crown 6-Ether, and cas is 14098-24-9, its synthesis route is as follows.,14098-24-9

General procedure: The carbonyl substrate (0.1 g) is dissolved in 1-2 mL of anhydrous CHCl3 and 2.0 equiv of a benzocrown ether is added to the solution. To this mixture, CF3SO3H (8.0 equiv; H2SO4 may be used in some cases) is added dropwise with stirring. The reaction is stirred at room temperature for at least 2 h, after which, the mixture is poured over several grams of ice. The resulting solution is extracted three times with CHCl3. The organic phase is subsequently washed three times with water and dried over MgSO4 solution. Removal of the solvent provides the product.

With the complex challenges of chemical substances, we look forward to future research findings about 14098-24-9,belong chiral-catalyst compound

Reference£º
Article; Zielinski, Matthew E.; Tracy, Adam F.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1701 – 1704;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

New learning discoveries about 602-09-5

With the rapid development of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol

[1,1′-Binaphthalene]-2,2′-diol, cas is 602-09-5, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,602-09-5

A solution of 5.73 g (20 mmol) of (1,1′-binaphthyl) -2,2′-diol and 4.10 g (20 mmol) of p-TsOH were dissolved in 150 mL of toluene,The solution was stirred at 100 & lt; 0 & gt; C for 12 hours.The reaction solution was cooled to room temperature,Adding a potassium carbonate solution thereto,The organic layer was extracted three times by using 60 mL of ethyl acetate.The organic layer thus collected was dried with magnesium sulfate,The residue obtained after the solvent was evaporated from the silica gel column chromatography was used to separate and purify the residue,To obtain 3.76 g of intermediate I-1 (yield: 70%).The compounds thus produced were determined by using liquid chromatography-mass spectrometry (LC-MS).

With the rapid development of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol

Reference£º
Patent; Sanxing Display Co., Ltd.; Shen Wenji; Li Yinyong; Jin Rongguo; Po Junhe; Li Xiaorong; Zheng Enzai; Huang Xihuan; Jin Meigeng; Liang Chengjue; (89 pag.)CN106565689; (2017); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

 

The important role of 1121-22-8

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Name is trans-Cyclohexane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 1121-22-8, its synthesis route is as follows.,1121-22-8

To a solution containing 1,6-diisocyanatohexane (5.04 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals, Milwaukee, Wis.) and anhydrous tetrahydrofuran (100 milliliters) stirring at room temperature was added 1,4-butanediol vinyl ether (3.48 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals) and dibutyltin dilaurate (0.19 grams, 0.3 mmol; obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of about 65 C. for 25 minutes. The progress of the reaction was monitored by 1H-NMR spectroscopy for consumption of the 1,4-butanediol vinyl ether reactant, indicated by the disappearance of the -CH2OH multiplet, which appears at 3.5 ppm as a shoulder peak on the downfield end of the intermediate isocyanate product whose signal is located at 3.35-3.40 ppm. The mixture was cooled to about 15 C. internal temperature after which to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.71 grams, 15 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in anhydrous tetrahydrofuran (10 milliliters). The mixture was stirred for about 60 minutes while warming up to room temperature, and thickened to form a gelatinous slurry. FTIR spectroscopic analysis of a reaction sample showed little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Any residual isocyanate was quenched by addition of methanol (5 milliliters). The reaction mixture was then filtered by vacuum filtration to give a semi-solid product, which was subsequently stirred in hexane to ensure full precipitation. The solid product was filtered and dried in air to give 8.17 grams of a white powder (79 percent yield). The product was believed to be of the formulae 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 mHz) at high temperature (60 C.) and indicated the above structure with the following assigned peaks: 1.05-1.90 ppm (several multiplets, 16 H integration, 4 methylene protons from 1,4-butanediol vinyl ether portion, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 2.95 ppm (multiplet, 4 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O-); 3.2 ppm (broad singlet, 1 H integration, tertiary methane proton adjacent to urea group on cyclohexane ring); 3.70 ppm (multiplet, 2 H integration, NH(CO)O(CH2)4-O-C(Hc)C(Ha)(Hb)); 3.96 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 3.98 ppm (multiplet, 2 H integration, NH(CO)OCH2CH2CH2CH2-O-C(Hc)C(Ha)(Hb)); 4.20 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 5.60 ppm and 5.72 ppm (broad singlets, each 1 H integration, urea NH protons); 6.48 ppm (doublet of doublets, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 6.82 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for C: 59.80%, H: 9.15%, N: 12.31%; found for C: 59.36%, H: 9.53%, N: 12.58%.

With the complex challenges of chemical substances, we look forward to future research findings about trans-Cyclohexane-1,2-diamine

Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare