Thiobenzanilide

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

Procedure: First, 3.2 g of sodium ethoxide, 10 g of N-phenylthiobenzamide, and 60 mL of ethanol were put in a 300 mL three-neck flask, and this mixed solution was stirred at room temperature for 1 hour. Then, 3.7 mL of iodoethane was added to this mixed solution, and heated and stirred at 60° C. for 6 hours to be reacted. After the reaction, ethanol was distilled off under a reduced pressure to give a brown oily substance. This oily substance was dissolved in dichloromethane, and washed with water and then a saturated aqueous solution of sodium hydrogen carbonate. After the washing, anhydrous magnesium sulfate was added to the resulting organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline was prepared (a brown oily substance, crude yield: 110%). The synthetic scheme of Step 1 is shown by (a-5). heated stirred at 60° C. for 6 hours to be reacted was distilled off under a reduced pressure to give a brown oily substance washed with water After the washing, anhydrous magnesium sulfate was added to the resulting organic layer for drying The resulting mixture was subjected to gravity filtration the filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline was prepared (a brown oily substance, crude yield: 110%)

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

Procedure: Next, 3.2 g of sodium ethoxide, 10 g of N-phenylthiobenzamide, and 60 mL of ethanol were put in a 300 mL three-neck flask, and stirred at room temperature for 1 hour. Then, 3.7 mL of iodoethane was added to this mixture, and heated and stirred at 60° C. for 6 hours to be reacted. After the reaction, ethanol was distilled off under a reduced pressure to give an oily substance. This oily substance was dissolved in dichloromethane, and washed with water and then a saturated aqueous solution of sodium hydrogen carbonate. Anhydrous magnesium sulfate was added to the resulting organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline was prepared (a brown oily substance, crude yield: 110%). The synthetic scheme of Step 2 is shown by (b-3). heated stirred at 60° C. for 6 hours to be reacted was distilled off under a reduced pressure to give an oily substance washed with water Anhydrous magnesium sulfate was added to the resulting organic layer for drying The resulting mixture was subjected to gravity filtration the filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline was prepared (a brown oily substance, crude yield: 110%)

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

Procedure: First, 3.2 g of sodium ethoxide, 10 g of N-phenylthiobenzamide, and 60 mL of ethanol were put in a 300 mL three-neck flask, and stirred at room temperature for 1 hour. Then, 3.7 mL of iodoethane was added to this mixture, and the mixture was heated and stirred at 60° C. for 6 hours to be reacted. After the reaction, ethanol was distilled off under a reduced pressure to give an oily substance. This oily substance was dissolved in dichloromethane, and washed with water and then a saturated aqueous solution of sodium hydrogen carbonate. Then, anhydrous magnesium sulfate was added to the resulting organic layer for drying. The resulting mixture was subjected to gravity filtration, and the filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline was prepared (a brown oily substance, crude yield: 110%). The synthesis scheme of Step 1 is shown by (a-1). the mixture was heated stirred at 60° C. for 6 hours to be reacted was distilled off under a reduced pressure to give an oily substance washed with water Then, anhydrous magnesium sulfate was added to the resulting organic layer for drying The resulting mixture was subjected to gravity filtration the filtrate was concentrated, so that N-[(ethylsulfanyl)phenylmethylidene]aniline was prepared (a brown oily substance, crude yield: 110%) The synthesis scheme of Step 1