2-CHLORO-4-FLUOROBENZAMIDE

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

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

Procedure: 3.47 g (0.02 mol) of 2-chloro-4-fluorobenzamide and 7.2 g (0.022 mol) of 3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl isocyanate are melted for two hours at 180° C., in the presence of one drop of dibutyl-tin dilaurate. After the mixture has been cooled, the solid product is comminuted in hot methanol, and the product is filtered off under suction and dried. 7.2 g (76.5% of theory) of 1-(2-chloro-4-fluoro-benzoyl)-3-(3-chloro-4-(2-chloro-1,1,2-trifluoro-ethoxy)-phenyl)-urea of melting point 186° C. are obtained. After the mixture has been cooled the product is filtered off under suction dried

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

Procedure: 1.64 g (6 mmol) of 2-chloro-4-fluorobenzamide were dissolved in 3 ml of dichloromethane and, at 0° C. and under a nitrogen atmosphere, 0.8 ml (9.3 mmol) of oxalyl chloride was added, and the mixture was heated to reflux for 9 hours. The reaction mixture was concentrated under high vacuum and afforded 1.17 g (5.8 mmol) of the desired product, which was employed as solution in dichloromethane (1 mmol in 1.7 ml of solution) in stage b. the mixture was heated to reflux for 9 hours The reaction mixture was concentrated under high vacuum

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

Procedure: 1.64 g (6 mmol) of 2-chloro-4-fluorobenzamide were dissolved in 3 ml of dichloromethane and, at 0° C. and under a nitrogen atmosphere, 0.8 ml (9.3 mmol) of oxalyl chloride was added, and the mixture was heated to reflux for 9 hours. The reaction mixture was concentrated under high vacuum and afforded 1.17 g (5.8 mmol) of the desired product, which was employed as solution in dichloromethane (1 mmol in 1.7 ml of solution) in stage b. the mixture was heated to reflux for 9 hours The reaction mixture was concentrated under high vacuum

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

Procedure: 1.64 g (6 mmol) of 2-chloro-4-fluorobenzamide were dissolved in 3 ml of dichloromethane and, at 0° C. and under a nitrogen atmosphere, 0.8 ml (9.3 mmol) of oxalyl chloride was added, and the mixture was heated to reflux for 9 hours. The reaction mixture was concentrated under high vacuum and afforded 1.17 g (5.8 mmol) of the desired product, which was employed as solution in dichloromethane (1 mmol in 1.7 ml of solution) in stage b. the mixture was heated to reflux for 9 hours The reaction mixture was concentrated under high vacuum

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

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

Procedure: starting from 2-chloro-4-fluorobenzamide and triethyloxonium tetrafluoroborate there is obtained ethyl 2-chloro-4-fluorobenzimidate as an oil; 1H-NMR(CDCl3): 1.43 (t, CH3), 4.40 (q, CH2), 6.9-7.8 (3 aromatic H+NH).

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

Procedure: The same method as in Example 3 was conducted using 2,6-dimethyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-4-ol (Reference Example 2) instead of 6-methyl-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-4-ol (Reference Example 1) and was conducted using 4-carbamoyl-3-chloro-1-fluorobenzene instead of 1,3-difluorobenzene to give the objective compound. to give the objective compound

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

Procedure: 3.47 g (0.02 mol) of 2-chloro-4-fluorobenzamide and 7.2 g (0.022 mol) of 3-chloro-4-(2-chloro-1,1,2-trifluoroethoxy)-phenyl isocyanate are melted for two hours at 180° C., in the presence of one drop of dibutyl-tin dilaurate. After the mixture has been cooled, the solid product is comminuted in hot methanol, and the product is filtered off under suction and dried. 7.2 g (76.5% of theory) of 1-(2-chloro-4-fluoro-benzoyl)-3-(3-chloro-4-(2-chloro-1,1,2-trifluoro-ethoxy)-phenyl)-urea of melting point 186° C. are obtained. After the mixture has been cooled the product is filtered off under suction dried

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

Procedure: 1.64 g (6 mmol) of 2-chloro-4-fluorobenzamide were dissolved in 3 ml of dichloromethane and, at 0° C. and under a nitrogen atmosphere, 0.8 ml (9.3 mmol) of oxalyl chloride was added, and the mixture was heated to reflux for 9 hours. The reaction mixture was concentrated under high vacuum and afforded 1.17 g (5.8 mmol) of the desired product, which was employed as solution in dichloromethane (1 mmol in 1.7 ml of solution) in stage b. the mixture was heated to reflux for 9 hours The reaction mixture was concentrated under high vacuum

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

Procedure: 1.64 g (6 mmol) of 2-chloro-4-fluorobenzamide were dissolved in 3 ml of dichloromethane and, at 0° C. and under a nitrogen atmosphere, 0.8 ml (9.3 mmol) of oxalyl chloride was added, and the mixture was heated to reflux for 9 hours. The reaction mixture was concentrated under high vacuum and afforded 1.17 g (5.8 mmol) of the desired product, which was employed as solution in dichloromethane (1 mmol in 1.7 ml of solution) in stage b. the mixture was heated to reflux for 9 hours The reaction mixture was concentrated under high vacuum