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

HRID 62685

반응식

HRID 62685 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5a8d2f727f2b4103ace43af14fb3d904
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447030B2

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