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

HRID 220779

反応式

HRID 220779 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-e009fb4c82ad4e8794c0ab9b295570ea
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

関連ノート

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