반응 #955935

반응 방정식

thiosemicarbazide

4-ethyl-2-methoxybenzoic acid

EDCI

→

5-(4-ethyl-2-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione

수율 55.0%

용매

pyridine

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction was stirred at r.t. for 24 h
2. 2
   기타The mixture was evaporated to dryness
3. 3
   workup.ADDITIONdiluted with water
4. 4
   기타A white solid was collected
5. 5
   세척washed with water
6. 6
   온도heated
7. 7
   온도at reflux for 2 days
8. 8
   여과The suspension was filtered hot
9. 9
   온도the aqueous solution was cooled in ice
10. 10
    기타The solid was collected
11. 11
    세척washed with water
12. 12
    기타dried

실험 절차

To a solution of 4-ethyl-2-methoxybenzoic acid (example 18b) (1 g, 6.1 mmol) in pyridine (6 mL) was added EDCI (1.2 g, 6.3 mmol) and the suspension was stirred at r.t. for 2 h. Then thiosemicarbazide (547 mg, 6 mmol) was added and the reaction was stirred at r.t. for 24 h. The mixture was evaporated to dryness and then diluted with water. A white solid was collected and washed with water. The solid was suspended in aq. NaHCO3 (1M, 20 mL) and 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 collected washed with water and dried to give 5-(4-ethyl-2-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione as a white powder (55%). MS (M+H, 236).

출처