반응 #51895

반응 방정식

ethyl 2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

4-chlorobenzylamine

sodium methoxide

→

title compound

수율 69.6%

N-(4-chlorobenzyl)-2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

수율 69.6%

용매

methanol

methanol

methanol

반응 조건

후처리

1. 1
   기타during the reaction
2. 2
   여과the mixture was filtered
3. 3
   세척the collected solid was washed with methanol
4. 4
   기타dried in vacuo
5. 5
   기타leaving a white solid
6. 6
   온도cooled to room temperature
7. 7
   여과filtered

실험 절차

A solution of ethyl 2-(hydroxymethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (627 mg, 2.23 mmol), 4-chlorobenzylamine (2.0 mL, 16.4 mmol), 0.5 M sodium methoxide in methanol (25 mL, 8.92 mmol) and methanol (10 mL) was stirred under nitrogen in a tightly capped 250 mL round bottom flask at 50° C. for 24 hours. The initial solution slowly dropped a thick white precipitate during the reaction. After cooling to room temperature, the mixture was filtered, and the collected solid was washed with methanol and dried in vacuo, leaving a white solid. The crude solid was suspended in boiling methanol (200 mL), cooled to room temperature, and filtered, to give the title compound as a white powder (585 mg).

출처