2-chlorobenzamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.23 g (1.5 mmol) of 2-chlorobenzamide and 0.19 g (1.6 mmol, 1.1 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.28 g (1.5 mmol) of 2,5-dichloro-4-cyano aniline were successively added thereto, reacted for 2 hours and filtered to obtain 0.43 g (Yield 78%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.23 g (1.5 mmol) of 2-chlorobenzamide and 0.19 g (1.6 mmol, 1.1 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.28 g (1.5 mmol) of 2,5-dichloro-4-cyano aniline were successively added thereto, reacted for 2 hours and filtered to obtain 0.43 g (Yield 78%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.23 g (1.5 mmol) of 2-chlorobenzamide and 0.19 g (1.6 mmol, 1.1 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.28 g (1.5 mmol) of 2,3-dichloro-4-cyano aniline were successively added thereto, reacted for 2 hours and filtered to obtain 0.25 g (Yield 45%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.25 g (1.6 mmol) of 2-chlorobenzamide and 0.22 g (1.8 mol, 1.1 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.3 g (1.6 mmol) of 2-chloro-4-fluoro-3-trifluoromethyl aniline were successively added thereto, reacted for 2 hours and filtered to obtain 0.53 g (Yield 84%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.42 g (2.7 mmol) of 2-chlorobenzamide and 0.36 g (2.9 mmol, 1.1 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.7 g (2.7 mmol) of 2-bromo-4-fluoro-5-trifluoromethyl aniline were successively added thereto, reacted for 2 hours and filtered to obtain 1.0 g (Yield 84%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.47 g (3.0 mmol) of 2-chlorobenzamide and 0.40 g (3.2 mmol, 1.05 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.95 g (3.0 mmol) of 2,4-dibromo-5-trifluoromethyl aniline were successively added thereto, reacted for 2 hours and filtered to obtain 1.2 g (Yield 80%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.47 g (3.0 mmol) of 2-chlorobenzamide and 0.40 g (3.2 mmol, 1.05 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.95 g (3.0 mmol) of 2,4-dibromo-5-trifluoromethyl aniline were successively added thereto, reacted for 2 hours and filtered to obtain 1.2 g (Yield 80%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.39 g (2.5 mmol) of 2-chlorobenzamide and 0.38 g (3.0 mmol, 1.2 eq) of oxalyl chloride were added to 10 ml of 1,2-dichloroethane and then the mixture was stirred for 8 hours at 100° C. The reaction solution was cooled down to room temperature. The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure to obtain 2-chlorobenzoyl isocyanate in an oily state. 10 ml of fresh 1,2-dichloroethane and 0.69 g (2.5 mmol) of 2-bromo-4-chloro-5-trifluoromethyl aniline were successively added thereto, reacted for 2 hours and filtered to obtain 0.61 g (Yield 53%) of the title compound as a solid. The reaction solution was cooled down to room temperature The reaction solvent and excessive oxalyl chloride were removed by distillation under reduced pressure

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

Procedure: In a manner similar to Step D of Example 1, the reaction of 0.58 g (0.0037 mole) 2-chlorobenzamide, 0.52 g (0.0051 mole) oxalyl chloride, 0.95 g (0.0037 mole) 5-amino-7-chloro-2,2,3,3-tetrafluoro-2,3-dihydrobenzothiophene, and 5 ml of methylene chloride in 75 ml of toluene produced 0.84 g of N-[[(7-chloro-2,2,3,3-tetrafluorobenzothien-5-yl)amino]-carbonyl]-2-chlorobenzamide as a solid (mp 140°-142° C.), compound 9 of Table 1.