N-phenylethanethioamide

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

Procedure: First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put into a round-bottom flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried over magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography using ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was obtained (a pale yellow powder, 18% yield). A scheme of the synthesis of Step 1 is shown in the following (c-1). provided with a reflux pipe to be heated the organic layer was extracted with dichloromethane The obtained organic layer was washed with water dried over magnesium sulfate The solution which had been dried was filtered The solvent of this solution was distilled off the resulting residue was purified by silica gel column chromatography

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

Procedure: First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put in a round-bottomed flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography which uses ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviated as HMptz) was obtained (pale yellow powder, yield: 18%). A scheme of the synthesis of Step 1 is shown below. provided with a reflux pipe This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated an organic layer was extracted with dichloromethane The obtained organic layer was washed with water dried with magnesium sulfate After the drying, the solution was filtrated The solvent of this solution was distilled off the resulting residue was purified by silica gel column chromatography which

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

Procedure: First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put in a round-bottomed flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography which uses ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviated as HMptz) was obtained (pale yellow powder, yield: 18%). A scheme of the synthesis of Step 1 is shown below. provided with a reflux pipe This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated an organic layer was extracted with dichloromethane The obtained organic layer was washed with water dried with magnesium sulfate After the drying, the solution was filtrated The solvent of this solution was distilled off the resulting residue was purified by silica gel column chromatography which

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

Procedure: First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put in a round-bottomed flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography which uses ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviated as HMptz) was obtained (pale yellow powder, yield: 18%). A scheme of the synthesis of Step 1 is shown below. provided with a reflux pipe This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated an organic layer was extracted with dichloromethane The obtained organic layer was washed with water dried with magnesium sulfate After the drying, the solution was filtrated The solvent of this solution was distilled off the resulting residue was purified by silica gel column chromatography which

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

Procedure: Next, 4.5 g of sodium ethoxide, 9.8 g of thioacetanilide, and 50 mL of ethanol were put in a 100 mL three-neck flask, and stirred at room temperature for 1 hour. Then, 5.3 mL of iodoethane was added to this mixture, and heated and stirred at 60° C. for 5 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. Anhydrous magnesium sulfate was added to the resulting organic layer for drying. After the drying, the solution was subjected to gravity filtration. The resulting filtrate was concentrated, so that N-[1-(ethylsulfanyl)ethylidene]aniline was prepared (a brown solid, yield: 73%). The synthetic scheme of Step 2 is shown by (b-2). heated stirred at 60° C. for 5 hours to be reacted was distilled off under a reduced pressure to give a brown oily substance washed with water Anhydrous magnesium sulfate was added to the resulting organic layer for drying After the drying, the solution was subjected to gravity filtration The resulting filtrate was concentrated, so that N-[1-(ethylsulfanyl)ethylidene]aniline was prepared (a brown solid, yield: 73%)

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

Procedure: First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put in a round-bottomed flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and an organic layer was extracted from dichloromethane. The organic layer was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography which uses ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was prepared (light yellow powder, yield: 18%). The synthetic scheme of Step 1 is shown by (a-1). provided with a reflux pipe This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to be heated an organic layer was extracted from dichloromethane The organic layer was washed with water dried with magnesium sulfate After the drying, the solution was filtrated The solvent of this solution was distilled off the resulting residue was purified by silica gel column chromatography which so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was prepared (light yellow powder, yield: 18%)

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

Procedure: First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put in a round-bottom flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to perform heating. Then, water was added to this solution and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried over magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography which uses ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was obtained (pale yellow powder, 18% yield). The synthesis scheme of Step 1 is shown below. provided with a reflux pipe This reaction container was subjected to irradiation with a microwave (2.45 GHz, 100 W) for 2 hours and 45 minutes to perform heating an organic layer was extracted with dichloromethane The obtained organic layer was washed with water dried over magnesium sulfate After the drying, the solution was filtered The solvent of this solution was distilled off the resulting residue was purified by silica gel column chromatography which

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

Procedure: First, 5.04 g of thioacetanilide, 5.44 g of benzoylhydrazine, and 50 mL of 1-butanol were put into a round-bottom flask provided with a reflux pipe, and the air in the flask was replaced with argon. This reaction container was irradiated with microwaves (2.45 GHz, 100W) for 2 hours and 45 minutes to be heated. Then, water was added to this solution and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with water and dried over magnesium sulfate. The solution which had been dried was filtered. The solvent of this solution was distilled off, and the resulting residue was purified by silica gel column chromatography using ethyl acetate as a developing solvent, so that 3-methyl-4,5-diphenyl-4H-1,2,4-triazole (abbreviation: HMptz) was obtained (a pale yellow powder, 18% yield). A scheme of the synthesis of Step 1 is shown in the following (c-1). provided with a reflux pipe to be heated the organic layer was extracted with dichloromethane The obtained organic layer was washed with water dried over magnesium sulfate The solution which had been dried was filtered The solvent of this solution was distilled off the resulting residue was purified by silica gel column chromatography