Isopropyl isocyanate → Tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamate

HRID 62685

反応式

HRID 62685 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[CH:21]([N:24]=[C:25]=[O:26])([CH3:23])[CH3:22]>ClCCl.O>[CH:21]([NH:24][C:25](=[O:26])[NH:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

参加物

5

反応物 2

HCID 61277Isopropyl isocyanateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

生成物 1

HCID 71007316Tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamate収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (0.20 g, 0.70 mmol, 1.0 equiv.) in dichloromethane (4 mL) was added isopropyl isocyanate (0.07 mL, 0.83 mmol, 1.2 equiv.) and TEA (0.19 mL, 1.37 mmol) at 0° C. The reaction was stirred at room temperature for 16 h. The reaction was then diluted with dichloromethane and water. The organic layer was separated, washed with water and brine, dried over sodium sulfate, then concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 20% EtOAc/hexanes) to give tert-butyl (2-(3-isopropylureido)-4-(thiophen-2-yl)phenyl)carbamate (0.18 g, 70% yield).

後処理

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography (silica gel, 20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-5a8d2f727f2b4103ace43af14fb3d904
出典データセット
uspto-grants-2016_09
特許番号
US09447030B2

関連ノート

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