Water → Methyl N-(4-methylpyridin-3-yl)carbamate

HRID 1853375

반응식

HRID 1853375 반응식
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14].[C:15](=O)([O:18]C)[O:16][CH3:17].O>O1CCCC1.C(OCC)(=O)C>[CH3:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:18])[O:16][CH3:17]

참가 물질

7

반응물 4

HCID 962WaterHCID 12021Dimethyl CarbonateHCID 1379353-Amino-4-picolineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 11672725Methyl N-(4-methylpyridin-3-yl)carbamate수율 74%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

At about 0° C., potassium tert-butoxide (47 g, 420 mmol, 3.00 equiv.) was added in several batches to a solution of 4-methylpyridin-3-amine (15 g, 139 mmol, 1.00 equiv.) in tetrahydrofuran (400 mL). After stifling the solution for about 30 minutes, dimethyl carbonate (18.8 g, 209 mmol, 1.50 equiv.) was then added. The solution was stirred at ambient temperature for about 16 hours and then water (100 mL) was added. Following standard extractive workup with ethyl acetate (3×200 mL), the crude product was purified by re-crystallization from ethyl acetate/petroleum ether (1:1) to give the title product as a pale yellow solid (17 g; yield=74%). LC-MS: m/z=167 (M+H)+.

후처리

  1. customfor about 30 minutes
  2. customthe crude product was purified by re-crystallization from ethyl acetate/petroleum ether (1:1)

출처 및 근거

ORD 기록
ord-db0a41d75a3b433dbf0fb0ee56502b9c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962638B2

연결된 노트

불러오는 중…