Reacción #43303

Ecuación de reacción

4-amino-3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole

4-methyl-3-nitrobenzoyl chloride

→

title compound

Rendimiento 87.9%

6-(4-Methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

Rendimiento 87.9%

Disolventes

phosphoryl chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 3 h
2. 2
   OtroThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (20 mL)
4. 4
   SecadoThe organic layer was dried over sodium sulfate
5. 5
   Concentraciónconcentrated

Procedimiento

A mixture of 4-amino-3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole (220 mg, 0.78 mmol) and 4-methyl-3-nitrobenzoyl chloride (156 mg, 0.78 mmol) in phosphoryl chloride (2 mL) was refluxed for 3 h. The solvent was evaporated and the residue was dissolved in dichloromethane (20 mL). It was neutralized by aqueous sodium carbonate. The organic layer was dried over sodium sulfate, and concentrated to give 293 mg (85%) of the title compound as solid. 1H NMR (CDCl3): 8.59 (d, J=2.1 Hz, 1H), 8.05-8.01 (dd, J=7.8, 1.8 Hz, 1H), 7.73 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 4.02 (s, 6H), 3.95 (s, 3H), 2.75 (s, 3H).

Fuente