Reaction #955909

Reaction equation

thiosemicarbazide

2-methoxy-4-methylbenzoic acid

EDCI

→

powder

Yield 47.0%

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

Yield 47.0%

Solvents

pyridine

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction was stirred at r.t. for 21 h
2. 2
   OtherThe mixture was evaporated to dryness
3. 3
   workup.ADDITIONdiluted with water
4. 4
   FiltrationThe white solid was then filtered
5. 5
   Washwashed with water
6. 6
   Temperatureheated
7. 7
   Temperatureat reflux for 2 days
8. 8
   FiltrationThe suspension was filtered hot
9. 9
   Temperaturethe aqueous solution was cooled in ice
10. 10
    FiltrationThe solid was filtered
11. 11
    Washwashed with water
12. 12
    Otherdried

Procedure

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%).

Source