1-bromo-1-phenylpropan-2-one

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:0.00; pressure:0.00; stir:

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

実験手順: 1-Bromo-1-phenyl-2-propanone (10.6g, 0.050 mole), o-chlorothiobenzamide (8.8g, 0.051 mole), and ethanol (100 ml) are mixed and, after the initial exothermic reaction has subsided, heated under reflux for two hours. The ethanol is evaporated and the residue is treated with chloroform and aqueous sodium bicarbonate. The chloroform layer is separated and evaporated to leave a yellow oil which solidifies on standing. Recrystallization from acetonitrile yields 11.3g (79%) of 2-(2-chlorophenyl)-4-methyl-5-phenylthiazole, m.p. 63°-65° C. after the initial exothermic reaction heated under reflux for two hours The ethanol is evaporated the residue is treated with chloroform and aqueous sodium bicarbonate The chloroform layer is separated evaporated to leave a yellow oil which Recrystallization from acetonitrile

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

実験手順: 1-Bromo-1-phenyl-2-propanone (10.6g, 0.050 mole), o-chlorothiobenzamide (8.8g, 0.051 mole), and ethanol (100 ml) are mixed and, after the initial exothermic reaction has subsided, heated under reflux for two hours. The ethanol is evaporated and the residue is treated with chloroform and aqueous sodium bicarbonate. The chloroform layer is separated and evaporated to leave a yellow oil which solidifies on standing. Recrystallization from acetonitrile yields 11.3g (79%) of 2-(2-chlorophenyl)-4-methyl-5-phenylthiazole, m.p. 63°-65° C. after the initial exothermic reaction heated under reflux for two hours The ethanol is evaporated the residue is treated with chloroform and aqueous sodium bicarbonate The chloroform layer is separated evaporated to leave a yellow oil which Recrystallization from acetonitrile

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

実験手順: 1-Bromo-1-phenyl-2-propanone (10.6g, 0.050 mole), o-chlorothiobenzamide (8.8g, 0.051 mole), and ethanol (100 ml) are mixed and, after the initial exothermic reaction has subsided, heated under reflux for two hours. The ethanol is evaporated and the residue is treated with chloroform and aqueous sodium bicarbonate. The chloroform layer is separated and evaporated to leave a yellow oil which solidifies on standing. Recrystallization from acetonitrile yields 11.3g (79%) of 2-(2-chlorophenyl)-4-methyl-5-phenylthiazole, m.p. 63°-65° C. after the initial exothermic reaction heated under reflux for two hours The ethanol is evaporated the residue is treated with chloroform and aqueous sodium bicarbonate The chloroform layer is separated evaporated to leave a yellow oil which Recrystallization from acetonitrile

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution of 132 μL (1.00 mmol) of phenylacetyl chloride in 1.0 mL of anhyd MeCN was added 1.05 mL (2.10 mmol) of a 2 M solution of trimethylsilyldiazomethane in hexane. After stirring 1 h at room temperature, the mixture was cooled (0° C.) and 300 μL (1.50 mmol) of 30 wt % HBr in acetic acid was added dropwise (gas evolution). After stirring 15 min, the mixture was concentrated in vacuo and rapidly chromatographed on a 2 g silica SPE column (Waters Sep-Pak) with 50% CH2Cl2-hexane to afford the title compound as a pale yellow oil (201 mg, 94%). 1H-NMR (300 MHz, CDCl3) δ7.2-7.4 (m, 5H), 3.95 (s, 2H), 3.92 (s, 2H). was added dropwise (gas evolution) After stirring 15 min the mixture was concentrated in vacuo rapidly chromatographed on a 2 g silica SPE column (Waters Sep-Pak) with 50% CH2Cl2-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 132 μL (1.00 mmol) of phenylacetyl chloride in 1.0 mL of anhyd MeCN was added 1.05 mL (2.10 mmol) of a 2 M solution of trimethylsilyldiazomethane in hexane. After stirring 1 h at room temperature, the mixture was cooled (0° C.) and 300 μL (1.50 mmol) of 30 wt % HBr in acetic acid was added dropwise (gas evolution). After stirring 15 min, the mixture was concentrated in vacuo and rapidly chromatographed on a 2 g silica SPE column (Waters Sep-Pak) with 50% CH2Cl2-hexane to afford the title compound as a pale yellow oil (201 mg, 94%). 1H-NMR (300 MHz, CDCl3) δ7.2-7.4 (m, 5H), 3.95 (s, 2H), 3.92 (s, 2H). was added dropwise (gas evolution) After stirring 15 min the mixture was concentrated in vacuo rapidly chromatographed on a 2 g silica SPE column (Waters Sep-Pak) with 50% CH2Cl2-hexane

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

実験手順: Reaction of 3-amino-5-butyl-4-[(2'-cyanobiphenyl-4-yl)methyl]-4H-1,2,4-triazole (from Example 1, Step D) with 1-bromo-1-phenylacetone [A. C. B. Smith and W. Wilson, J. Chem. Soc., 1342 (1955)] according to the procedure of Example 1, Step E, gave an essentially quantitiative yield of the title compound as a yellow oil, suitable for use in the next step.

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

実験手順: 1-Bromo-1-phenyl-2-propanone (10.6 g, 0.050 mole), o-chlorothiobenzamide (8.8 g, 0.051 mole), and ethanol (100 ml) are mixed and, after the initial exothermic reaction has subsided, heated under reflux for two hours. The ethanol is evaporated and the residue is treated with chloroform and aqueous sodium bicarbonate. The chloroform layer is separated and evaporated to leave a yellow oil which solidifies on standing. Recrystallization from acetonitrile yields 11.3 g (79%) of 2-(2-chlorophenyl)-4-methyl-5-phenylthiazole, m.p. 63°-65° C. after the initial exothermic reaction heated under reflux for two hours The ethanol is evaporated the residue is treated with chloroform and aqueous sodium bicarbonate The chloroform layer is separated evaporated to leave a yellow oil which Recrystallization from acetonitrile

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

実験手順: To N(1-phenoxy-2-propyl)piperazine (1 mole) dissolved in methylethylketone (1000 ml) are added dry potassium carbonate (2 moles) and 1-bromo-1-phenyl-acetone (1 mole). The mixture is refluxed during 5 hours, with stirring. The solvent is evaporated off in vacuo. The residue is taken up into water and is then extracted with methylene chloride. The organic phase is washed with water to neutral pH. The organic phase is extracted with a dilute aqueous hydrochloric acid solution and is then concentrated in vacuo, over a water-bath. The resulting oil is taken up into boiling 95% ethyl alcohol, to give, on cooling, white crystals, M.p. 177°-180° C. N.M.R.: consistent. The mixture is refluxed during 5 hours The solvent is evaporated off in vacuo is then extracted with methylene chloride The organic phase is washed with water to neutral pH The organic phase is extracted with a dilute aqueous hydrochloric acid solution is then concentrated in vacuo, over a water-bath to give on cooling