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

HRID 2068995

反応式

HRID 2068995 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-6d0f64aa9ba24df1866ac5b506cb324e
出典データセット
uspto-grants-2012_10
特許番号
US08299084B2

関連ノート

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