Benzoyl chloride → 1-Benzoyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

HRID 220779

반응식

HRID 220779 반응식
[NH:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl.C(N(CC)CC)C.CCOC(C)=O>[C:13]([N:1]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 2

HCID 7412Benzoyl chlorideHCID 2947881,2,3,4-Tetrahydro-benzo(b)azepin-5-one

생성물 1

HCID 231123881-Benzoyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one수율 56%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

1,2,3,4-Tetrahydro-benzo[b]azepin-5-one from Example E5.5 (480 mg, 2.98 mmol) was dissolved in a mixture of dichloromethane (30 ml) and triethylamine (1.3 ml). Benzoyl chloride (0.46 g, 3.28 mmol) was added and the reaction mixture was heated for at reflux for 2 h. The mixture was cooled and reduced in vacuo. The residue was dissolved in EtOAc and washed with 1M KHSO4 (aq), water and brine. The organic layer was dried, filtered and reduced in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 50% EtOAc: 50% hexane) to yield the title compound (440 mg, 56%).

후처리

  1. temperaturethe reaction mixture was heated for
  2. temperatureat reflux for 2 h
  3. temperatureThe mixture was cooled
  4. washwashed with 1M KHSO4 (aq), water and brine
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customThe residue was purified by flash chromatography on silica gel (eluant; 50% EtOAc: 50% hexane)

출처 및 근거

ORD 기록
ord-e009fb4c82ad4e8794c0ab9b295570ea
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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