反応 #955935

反応方程式

thiosemicarbazide

4-ethyl-2-methoxybenzoic acid

EDCI

→

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

収率 55.0%

溶媒

pyridine

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction was stirred at r.t. for 24 h
2. 2
   その他The mixture was evaporated to dryness
3. 3
   workup.ADDITIONdiluted with water
4. 4
   その他A white solid was collected
5. 5
   洗浄washed with water
6. 6
   温度heated
7. 7
   温度at reflux for 2 days
8. 8
   ろ過The suspension was filtered hot
9. 9
   温度the aqueous solution was cooled in ice
10. 10
    その他The solid was collected
11. 11
    洗浄washed with water
12. 12
    その他dried

実験手順

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).

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