Ethyl chloroformate → Tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate

HRID 2201685

반응식

HRID 2201685 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].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCl.CN(C1C=CN=CC=1)C.O>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:6]1[CH:5]=[CH:4][C:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[C:2]([NH:1][C:22](=[O:23])[O:24][CH2:25][CH3:26])[CH:7]=1

참가 물질

6

반응물 2

HCID 10928Ethyl chloroformateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

생성물 1

HCID 71007309Tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate수율 44%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (0.20 g, 0.69 mmol, 1.0 equiv.) in dichloromethane (4 mL) was added ethyl chloroformate (0.08 mL, 0.83 mmol, 1.2 equiv.), TEA (0.19 mL, 1.37 mmol, 2.0 equiv.) and DMAP (8 mg, 0.07 mmol, 0.1 equiv.) at 0° C. The reaction was warmed to room temperature and stirred 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, filtered and concentrated under reduced pressure. The crude material was purified on column chromatography (silica gel, 20% EtOAc/hexanes) to give tert-butyl ethyl (4-(thiophen-2-yl)-1,2-phenylene)dicarbamate (0.11 g, 44% yield).

후처리

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

출처 및 근거

ORD 기록
ord-db55e1f2f4cb4fb69d87d452b8104580
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365498B2

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