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

HRID 220779
Notes
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Reaction equation

HRID 220779 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e009fb4c82ad4e8794c0ab9b295570ea
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202858B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes