Reacción #955909

Ecuación de reacción

thiosemicarbazide

2-methoxy-4-methylbenzoic acid

EDCI

→

powder

Rendimiento 47.0%

5-(2-methoxy-4-methylphenyl)-2H-1,2,4-triazole-3(4H)-thione

Rendimiento 47.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was stirred at r.t. for 21 h
2. 2
   OtroThe mixture was evaporated to dryness
3. 3
   workup.ADDITIONdiluted with water
4. 4
   FiltraciónThe white solid was then filtered
5. 5
   Lavadowashed with water
6. 6
   Temperaturaheated
7. 7
   Temperaturaat reflux for 2 days
8. 8
   FiltraciónThe suspension was filtered hot
9. 9
   Temperaturathe aqueous solution was cooled in ice
10. 10
    FiltraciónThe solid was filtered
11. 11
    Lavadowashed with water
12. 12
    Otrodried

Procedimiento

To a solution of 2-methoxy-4-methylbenzoic acid (1.81 g, 9.22 mmol) in 9 ml of pyridine was added EDCI (1.9 g, 9.3 mmol) and the suspension was stirred at r.t. for 1 h. Then thiosemicarbazide (800 mg, 8.8 mmol) was added and the reaction was stirred at r.t. for 21 h. The mixture was evaporated to dryness and then diluted with water. The white solid was then filtered, washed with water and suspended in 20 ml 1 M aq. NaHCO3 and then heated at reflux for 2 days. The suspension was filtered hot and the aqueous solution was cooled in ice and acidified to pH 3 with conc. HCl. The solid was filtered and washed with water and dried to give a white powder (47%).

Fuente