1-(isothiocyanatomethyl)-4-methoxybenzene

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

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

Procedure: Furan-2-ylmethylamine (190 mg) was dissolved in dimethylformamide (5 ml) and to the solution were added triethylamine (200 mg) and 4-methoxybenzylisothiocyanate (360 mg), followed by stirring at room temperature for 24 hours. Then, the resulting mixture was diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by column-chromatography (hexane/ethyl acetate=1/1) to yield the compound 16-1 (0.5 g, 90%) as a liquid. washed with water dried concentrated under reduced pressure The residue was purified by column-chromatography (hexane/ethyl acetate=1/1)

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

Procedure: Furan-2-ylmethylamine (190 mg) was dissolved in dimethylformamide (5 ml) and to the solution were added triethylamine (200 mg) and 4-methoxybenzylisothiocyanate (360 mg), followed by stirring at room temperature for 24 hours. Then, the resulting mixture was diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by column-chromatography (hexane/ethyl acetate=1/1) to yield the compound 16-1 (0.5 g, 90%) as a liquid. washed with water dried concentrated under reduced pressure The residue was purified by column-chromatography (hexane/ethyl acetate=1/1)

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

Procedure: A solution of 1H-indole-5-carbohydrazide (0.7 g, 3.98 mmol) and 1-isothiocyanatomethyl-4-methoxy-benzene (1.0 g, 5.56 mmol) in EtOH (10 mL) was heated to reflux for 2 h. The solvent was then removed in vacuo and the residue was triturated with EtOH (5 mL) to give 2-(1H-indole-5-carbonyl)-N-(4-methoxybenzyl)-hydrazinecarbothioamide (0.7 g, 2.0 mmol, 51%) as a white solid. MS (ESI, pos. ion) m/z: 355 (M+1). to reflux for 2 h The solvent was then removed in vacuo the residue was triturated with EtOH (5 mL)

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

Procedure: A solution of 1H-indole-5-carbohydrazide (0.7 g, 3.98 mmol) and 1-isothiocyanatomethyl-4-methoxy-benzene (1.0 g, 5.56 mmol) in EtOH (10 mL) was heated to reflux for 2 h. The solvent was then removed in vacuo and the residue was triturated with EtOH (5 mL) to give 2-(1H-indole-5-carbonyl)-N-(4-methoxybenzyl)-hydrazinecarbothioamide (0.7 g, 2.0 mmol, 51%) as a white solid. MS (ESI, pos. ion) m/z: 355 (M+1). to reflux for 2 h The solvent was then removed in vacuo the residue was triturated with EtOH (5 mL)

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

Procedure: A solution of p-methoxybenzyl isothiocyanate (8.95 g.) and the ethyl ester of oxalic acid monohydrazide (6.8 g.) in ethanol (50 ml.) was refluxed for a period of approximately 16 hours (overnight). The hot solution was then filtered, the filtrate evaporated in vacuo and the resulting oil triturated with dry diethyl ester. The solid product so obtained, viz., 3-ethoxycarbonyl-4-(p-methoxybenzyl)-1,2,4-triazole-5-thiol (yield, 7.2 g.) was then recrystallized from ethanol-water to yield 4.0 g. of pure material. The analytical sample melted at 142°-144° C. after a further recrystallization from ethyl acetate/petroleum ether (b.p. 60°-80° C.). The hot solution was then filtered the filtrate evaporated in vacuo the resulting oil triturated with dry diethyl ester The solid product so obtained , 3-ethoxycarbonyl-4-(p-methoxybenzyl)-1,2,4-triazole-5-thiol (yield, 7.2 g.) was then recrystallized from ethanol-water to yield 4.0 g The analytical sample melted at 142°-144° C. after a further recrystallization from ethyl acetate/petroleum ether (b.p. 60°-80° C.)

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

Procedure: A solution of p-methoxybenzyl isothiocyanate (8.95 g.) and the ethyl ester of oxalic acid monohydrazide (6.8 g.) in ethanol (50 ml.) was refluxed for a period of approximately 16 hours (overnight). The hot solution was then filtered, the filtrate evaporated in vacuo and the resulting oil triturated with dry diethyl ester. The solid product so obtained, viz., 3-ethoxycarbonyl-4-(p-methoxybenzyl)-1,2,4-triazole-5-thiol (yield, 7.2 g.) was then recrystallized from ethanol-water to yield 4.0 g. of pure material. The analytical sample melted at 142°-144° C. after a further recrystallization from ethyl acetate/petroleum ether (b.p. 60°-80° C.). The hot solution was then filtered the filtrate evaporated in vacuo the resulting oil triturated with dry diethyl ester The solid product so obtained , 3-ethoxycarbonyl-4-(p-methoxybenzyl)-1,2,4-triazole-5-thiol (yield, 7.2 g.) was then recrystallized from ethanol-water to yield 4.0 g The analytical sample melted at 142°-144° C. after a further recrystallization from ethyl acetate/petroleum ether (b.p. 60°-80° C.)

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

Procedure: This compound was synthesized using the same methodology as described in Example 1 above, using 2-furancarboxylic acid hydrazide, 4-methoxybenzyl isothiocyanate and benzyl bromide as the starting materials. This compound was synthesized

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

Procedure: This compound was synthesized using the same methodology as described in Example 1 above, using 2-furancarboxylic acid hydrazide, 4-methoxybenzyl isothiocyanate and 4-trifluoromethylbenzyl bromide as the starting materials. (M+H)+−446. This compound was synthesized

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

Procedure: This compound was synthesized using the same methodology as described in Example 1 above, using 2-furancarboxylic acid hydrazide, 4-methoxybenzyl isothiocyanate and benzyl bromide as the starting materials. This compound was synthesized

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

Procedure: This compound was synthesized using the same methodology as described in Example 1 above, using 2-furancarboxylic acid hydrazide, 4-methoxybenzyl isothiocyanate and 4-trifluoromethylbenzyl bromide as the starting materials. (M+H)+−446. This compound was synthesized

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