4-chloro-N-cyclohexylbenzamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Cyclohexyl 4-chlorobenzamide (12.8 g, 53.9 mmole) and thionyl chloride (43.14 g, 363 mmole) were heated at reflux with stirring for 1.75 hours. Excess thionyl chloride was removed by distillation. The title compound was isolated by distillation (b.p. 130° C. at ~15 mm Hg) to yield 7.4 g (54%) of a clear colorless liquid which crystallized upon cooling. at reflux Excess thionyl chloride was removed by distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cold solution of 9.6 gm. (0.096 mole) of phosgene in tetrahydrofuran is added in one portion 19.0 gm. (0.08 mole) of N-cyclohexyl-p-chlorobenzamide. After ten minutes the reaction mixture is allowed to warm to room temperature, stirred overnight, and the mixture concentrated to a solid in vacuo with a bath temperature of 30°. The crude residue is suspended in 250 ml. of acetonitrile, cooled to 0° and treated with a solution of 28.0 gm. (0.32 mole) of morpholine in 100 ml. of acetonitrile. After allowing the reaction mixture to warm to room temperature it is heated at reflux for two hours, concentrated in vacuo to an oil and suspended in ether. A precipitate is collected and shown to be starting material. The filtrate is concentrated in vacuo, the residue taken up in acetone and treated with excess dry HCl in ether. Ether is added to the cloud point and the mixture cooled to give 3.7 gm. (13.5%) m.p. 278°-279°. After ten minutes the reaction mixture is allowed the mixture concentrated to a solid in vacuo with a bath temperature of 30° of acetonitrile, cooled to 0° treated with a solution of 28.0 gm to warm to room temperature it is heated at reflux for two hours concentrated in vacuo to an oil A precipitate is collected The filtrate is concentrated in vacuo treated with excess dry HCl in ether Ether is added to the cloud point the mixture cooled to give 3.7 gm

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cold solution of 9.6 gm. (0.096 mole) of phosgene in tetrahydrofuran is added in one portion 19.0 gm. (0.08 mole) of N-cyclohexyl-p-chlorobenzamide. After ten minutes the reaction mixture is allowed to warm to room temperature, stirred overnight, and the mixture concentrated to a solid in vacuo with a bath temperature of 30°. The crude residue is suspended in 250 ml. of acetonitrile, cooled to 0° and treated with a solution of 28.0 gm. (0.32 mole) of morpholine in 100 ml. of acetonitrile. After allowing the reaction mixture to warm to room temperature it is heated at reflux for two hours, concentrated in vacuo to an oil and suspended in ether. A precipitate is collected and shown to be starting material. The filtrate is concentrated in vacuo, the residue taken up in acetone and treated with excess dry HCl in ether. Ether is added to the cloud point and the mixture cooled to give 3.7 gm. (13.5%) m.p. 278°-279°. After ten minutes the reaction mixture is allowed the mixture concentrated to a solid in vacuo with a bath temperature of 30° of acetonitrile, cooled to 0° treated with a solution of 28.0 gm to warm to room temperature it is heated at reflux for two hours concentrated in vacuo to an oil A precipitate is collected The filtrate is concentrated in vacuo treated with excess dry HCl in ether Ether is added to the cloud point the mixture cooled to give 3.7 gm

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexylamine (80 gm., 0.8 mole) is dissolved in 2.5 l. of benzene and treated dropwise with 70 gm. (0.4 mole) of p-chlorobenzoyl chloride in 250 ml. of benzene over 45 minutes with intermittent cooling to maintain reaction temperature between 22°-30°. After stirring an additional 15 minutes, the mixture is diluted with benzene and washed with water. A suspended solid is filtered and the filtrate concentrated to 1 l. to give a second crop; these are combined and recrystallized from methanol, 65.0 gm. (68.5%), m.p. 191°-193°. to maintain reaction temperature between 22°-30° washed with water A suspended solid is filtered the filtrate concentrated to 1 l to give a second crop recrystallized from methanol, 65.0 gm

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Cyclohexyl 4-chlorobenzamide (12.8 g, 53.9 mmole) and thionyl chloride (43.14 g, 363 mmole) were heated at reflux with stirring for 1.75 hours. Excess thionyl chloride was removed by distillation. The title compound was isolated by distillation (b.p. 130° C. at ~15 mm Hg) to yield 7.4 g (54%) of a clear colorless liquid which crystallized upon cooling. at reflux Excess thionyl chloride was removed by distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Cyclohexyl 4-chlorobenzamide (12.8 g, 53.9 mmole) and thionyl chloride (43.14 g, 363 mmole) were heated at reflux with stirring for 1.75 hours. Excess thionyl chloride was removed by distillation. The title compound was isolated by distillation (b.p. 130° C. at ~15 mm Hg) to yield 7.4 g (54%) of a clear colorless liquid which crystallized upon cooling. at reflux Excess thionyl chloride was removed by distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cold solution of 9.6 gm. (0.096 mole) of phosgene in tetrahydrofuran is added in one portion 19.0 gm. (0.08 mole) of N-cyclohexyl-p-chlorobenzamide. After ten minutes the reaction mixture is allowed to warm to room temperature, stirred overnight, and the mixture concentrated to a solid in vacuo with a bath temperature of 30°. The crude residue is suspended in 250 ml. of acetonitrile, cooled to 0° and treated with a solution of 28.0 gm. (0.32 mole) of morpholine in 100 ml. of acetonitrile. After allowing the reaction mixture to warm to room temperature it is heated at reflux for two hours, concentrated in vacuo to an oil and suspended in ether. A precipitate is collected and shown to be starting material. The filtrate is concentrated in vacuo, the residue taken up in acetone and treated with excess dry HCl in ether. Ether is added to the cloud point and the mixture cooled to give 3.7 gm. (13.5%) m.p. 278°-279°. After ten minutes the reaction mixture is allowed the mixture concentrated to a solid in vacuo with a bath temperature of 30° of acetonitrile, cooled to 0° treated with a solution of 28.0 gm to warm to room temperature it is heated at reflux for two hours concentrated in vacuo to an oil A precipitate is collected The filtrate is concentrated in vacuo treated with excess dry HCl in ether Ether is added to the cloud point the mixture cooled to give 3.7 gm

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclohexylamine (80 gm., 0.8 mole) is dissolved in 2.5 l. of benzene and treated dropwise with 70 gm. (0.4 mole) of p-chlorobenzoyl chloride in 250 ml. of benzene over 45 minutes with intermittent cooling to maintain reaction temperature between 22°-30°. After stirring an additional 15 minutes, the mixture is diluted with benzene and washed with water. A suspended solid is filtered and the filtrate concentrated to 1 l. to give a second crop; these are combined and recrystallized from methanol, 65.0 gm. (68.5%), m.p. 191°-193°. to maintain reaction temperature between 22°-30° washed with water A suspended solid is filtered the filtrate concentrated to 1 l to give a second crop recrystallized from methanol, 65.0 gm

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Cyclohexyl 4-chlorobenzamide (12.8 g, 53.9 mmole) and thionyl chloride (43.14 g, 363 mmole) were heated at reflux with stirring for 1.75 hours. Excess thionyl chloride was removed by distillation. The title compound was isolated by distillation (b.p. 130° C. at ~15 mm Hg) to yield 7.4 g (54%) of a clear colorless liquid which crystallized upon cooling. at reflux Excess thionyl chloride was removed by distillation