4-chloro-2-methoxybenzamide

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: A solution of 4-chloro-2-methoxybenzamide (0.74 g, 3.99 mmol) in dichloromethane (50 ml) was cooled to −78° C. followed by addition of BBr3 (1.15 ml, 11.96 mmol) under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 2 h. After the completion of reaction (TLC monitoring), the solution was cooled to 0° C. and quenched with water. The resulting solution was basified by aqueous NaHCO3 and extracted with EtOAc (3×100 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated to get the desired product (0.608 g, 89%). MS: 172.33 (M+H)+. After the completion of reaction (TLC monitoring) the solution was cooled to 0° C. quenched with water extracted with EtOAc (3×100 ml) The combined organics was dried over anhydrous Na2SO4 filtered concentrated

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

実験手順: A solution of 4-chloro-2-methoxybenzamide (0.74 g, 3.99 mmol) in dichloromethane (50 ml) was cooled to −78° C. followed by addition of BBr3 (1.15 ml, 11.96 mmol) under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 2 h. After the completion of reaction (TLC monitoring), the solution was cooled to 0° C. and quenched with water. The resulting solution was basified by aqueous NaHCO3 and extracted with EtOAc (3×100 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated to get the desired product (0.608 g, 89%). MS: 172.33 (M+H)+. After the completion of reaction (TLC monitoring) the solution was cooled to 0° C. quenched with water extracted with EtOAc (3×100 ml) The combined organics was dried over anhydrous Na2SO4 filtered concentrated

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-chloro-2-methoxybenzamide (0.82 g, 4.42 mmol) in toluene (20 ml) was added chlorocarbonylsulfenyl chloride (0.73 ml, 8.84 mmol) under nitrogen atmosphere and the resulting reaction mixture was refluxed at 90° C. for 2 h. After the completion of the reaction (TLC monitoring) water was added followed by extraction with ether (3×50 ml). The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water. The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated to get desired product (1.03 g, 96% crude yield) that was carried forward as such without further purification. MS: 244.16 (M+H)+. the resulting reaction mixture was added followed by extraction with ether (3×50 ml) The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water The organic layer was then dried over anhydrous Na2SO4 filtered concentrated

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-chloro-2-methoxybenzamide (0.82 g, 4.42 mmol) in toluene (20 ml) was added chlorocarbonylsulfenyl chloride (0.73 ml, 8.84 mmol) under nitrogen atmosphere and the resulting reaction mixture was refluxed at 90° C. for 2 h. After the completion of the reaction (TLC monitoring) water was added followed by extraction with ether (3×50 ml). The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water. The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated to get desired product (1.03 g, 96% crude yield) that was carried forward as such without further purification. MS: 244.16 (M+H)+. the resulting reaction mixture was added followed by extraction with ether (3×50 ml) The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water The organic layer was then dried over anhydrous Na2SO4 filtered concentrated

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: In tetrahydrofuran (100 ml), 4-chloro-2-methoxybenzamide (5.67 g, 30.5 mmol) prepared in the Step 7-1-1 and chlorocarbonylsulfenyl chloride (4.40 g, 33.6 mmol) were suspended, and the mixture was heated under reflux for 1.5 hours. After being allowed to cool, the mixture was subjected to extraction with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1) to give the title compound (5.33 g, 71%). the mixture was heated under reflux for 1.5 hours to cool the mixture was subjected to extraction with ethyl acetate the extract was dried over anhydrous magnesium sulfate concentrated The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1)

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

実験手順: In tetrahydrofuran (100 ml), 4-chloro-2-methoxybenzamide (9.40 g, 50.6 mmol) prepared in the Step 7-1-1 and Lawesson's reagent (10.2 g, 25.3 mmol) were suspended, and the suspension was heated under reflux for 2 hours. After the suspension was allowed to cool, a saturated sodium bicarbonate solution was added to the suspension to stop the reaction. Then the reaction mixture was subjected to extraction with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (6.63 g, 65%) as a yellow powder. the suspension was heated under reflux for 2 hours to cool the reaction Then the reaction mixture was subjected to extraction with ethyl acetate the extract was dried over anhydrous magnesium sulfate concentrated The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)

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

実験手順: A solution of 4-chloro-2-methoxybenzamide (0.74 g, 3.99 mmol) in dichloromethane (50 ml) was cooled to −78° C. followed by addition of BBr3 (1.15 ml, 11.96 mmol) under nitrogen atmosphere. The reaction mixture was allowed to stir at room temperature for 2 h. After the completion of reaction (TLC monitoring), the solution was cooled to 0° C. and quenched with water. The resulting solution was basified by aqueous NaHCO3 and extracted with EtOAc (3×100 ml). The combined organics was dried over anhydrous Na2SO4, filtered and concentrated to get the desired product (0.608 g, 89%). MS: 172.33 (M+H)+. After the completion of reaction (TLC monitoring) the solution was cooled to 0° C. quenched with water extracted with EtOAc (3×100 ml) The combined organics was dried over anhydrous Na2SO4 filtered concentrated

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-chloro-2-methoxybenzamide (0.82 g, 4.42 mmol) in toluene (20 ml) was added chlorocarbonylsulfenyl chloride (0.73 ml, 8.84 mmol) under nitrogen atmosphere and the resulting reaction mixture was refluxed at 90° C. for 2 h. After the completion of the reaction (TLC monitoring) water was added followed by extraction with ether (3×50 ml). The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water. The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated to get desired product (1.03 g, 96% crude yield) that was carried forward as such without further purification. MS: 244.16 (M+H)+. the resulting reaction mixture was added followed by extraction with ether (3×50 ml) The combined organics was then sequentially washed with water, 10% NaHCO3 (aqueous solution) and finally again with water The organic layer was then dried over anhydrous Na2SO4 filtered concentrated