acetyl cyanide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Alternatively, 1-(4-bromophenyl)-2,2,2-trifluoroethanol (0.98 g, 3.86 mmol), m-tolylboronic acid (0.63 g, 4.63 mmol), Pd(PPh3)2Cl2 (0.16 g, 0.232 mmol Pd), Na2CO3 (0.90 g, 8.49 mmol), AcCN (10 mls), and H2O (10 mls) were combined and heated in the microwave at 150° C. for 10 minutes. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, concentrated, slurried in CH2Cl2, filtered, and chromatographed over silica gel (CH2Cl2) to give 0.80 g of 2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol. Yield: 79%. The mixture was cooled concentrated filtered chromatographed over silica gel (CH2Cl2)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of Example 100B (2.0 g, 0.0057 mol) and excess pyruvonitrile (2 mL) in xylene was heated at reflux in a pressure tube overnight. The solvent was removed and the residue was purified on silica gel (5˜30% ethyl acetate in hexane) to give 1.74 g of product as a light yellow solid (84% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (d, J=6.25 Hz, 6H) 2.77 (s, 3H) 4.46-4.61 (m, 1H) 6.89-6.99 (m, 2H) 7.18-7.25 (m, 2H) 8.03 (s, 1H). MS (ESI), M/Z: 394.0 (M+33)+. at reflux in a pressure tube overnight The solvent was removed the residue was purified on silica gel (5˜30% ethyl acetate in hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 6-hydroxytetralone (0.972 g, 6.0 mmol) in 10 mL of freshly distilled AcCN at room temperature was added sequentially dry NaI (2.25 g, 15 mmol), TEA (2.10 mL, 15 mmol), and chlorotrimethylsilane (1.92 mL, 15 mmol). After stirring for 1 hour, the reaction was quenched with the addition of a cold solution of saturated ammonium chloride and the reaction was extracted into Et2O (2×100 mL). The combined extracts were washed with ice cold water and then dried, filtered, and concentrated in vacuo to afford 1.53 g of the title compound as a colorless oil which was used for further reaction without purification. the reaction was quenched with the addition of a cold solution of saturated ammonium chloride the reaction was extracted into Et2O (2×100 mL) The combined extracts were washed with ice cold water dried filtered concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of 22.1 g of acetyl cyanide and 16.3 g of diaminomaleonitrile were added dropwise a solution of 0.5 g of phosphorus pentoxide in 3 ml of methanol. The crude product thus obtained was recrystallized from aqueous methanol to obtain 6.3 g (26% yield) of α-cyanoethylidenediaminomaleonitrile. The crude product thus obtained was recrystallized from aqueous methanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 10.8 g of diaminomaleonitrile and 10.0 g of acetyl cyanide were added successively to a solution of 1.9 g of p-toluenesulfonic acid in 100 ml of dry diethyl ether. The resulting yellow powder was collected by filtration and dried. The crude product thus obtained was dissolved in 600 ml of acetone and any insoluble insoluble solids were removed by filtration. 900 ml of water was added to the filtrate to obtain α-cyanoethylidenediaminomaleonitrile in 41% yield. The resulting yellow powder was collected by filtration dried The crude product thus obtained any insoluble insoluble solids were removed by filtration 900 ml of water was added to the filtrate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 16 g of diaminomaleonitrile and 12.6 g of acetyl cyanide was stirred with a glass rod whereby an exothermic reaction occurred and the resulting reaction mixture turned into a yellow-colored mixture. After allowing the mixture to stand for 10 minutes, the mixture was washed with small amount of cooled methanol and dried under reduced pressure to obtain 22.65 g (95.9% yield) of crude crystals of α-cynoethylidenediaminomaleonitrile which was found to have a purity sufficient to be used in subsequent reactions. For analysis, a sample of the above crystals was then repeatedly recrystallized from a mixture of methanol and water (3:2 by volume) to obtain α-cyanoethylidenediaminomaleonitrile having a melting point of 220°-221° C as milky white fine crystals. an exothermic reaction the resulting reaction mixture the mixture was washed with small amount of cooled methanol dried under reduced pressure to obtain 22.65 g (95.9% yield) of crude crystals of α-cynoethylidenediaminomaleonitrile which For analysis, a sample of the above crystals was then repeatedly recrystallized from a mixture of methanol and water (3:2 by volume)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Alternatively, 1-(4-bromophenyl)-2,2,2-trifluoroethanol (0.98 g, 3.86 mmol), m-tolylboronic acid (0.63 g, 4.63 mmol), Pd(PPh3)2Cl2 (0.16 g, 0.232 mmol Pd), Na2CO3 (0.90 g, 8.49 mmol), AcCN (10 mls), and H2O (10 mls) were combined and heated in the microwave at 150° C. for 10 minutes. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, concentrated, slurried in CH2Cl2, filtered, and chromatographed over silica gel (CH2Cl2) to give 0.80 g of 2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol. Yield: 79%. The mixture was cooled concentrated filtered chromatographed over silica gel (CH2Cl2)

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Alternatively, 1-(4-bromophenyl)-2,2,2-trifluoroethanol (0.98 g, 3.86 mmol), m-tolylboronic acid (0.63 g, 4.63 mmol), Pd(PPh3)2Cl2 (0.16 g, 0.232 mmol Pd), Na2CO3 (0.90 g, 8.49 mmol), AcCN (10 mls), and H2O (10 mls) were combined and heated in the microwave at 150° C. for 10 minutes. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, concentrated, slurried in CH2Cl2, filtered, and chromatographed over silica gel (CH2Cl2) to give 0.80 g of 2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol. Yield: 79%. The mixture was cooled concentrated filtered chromatographed over silica gel (CH2Cl2)