m-Chloroperbenzoic acid → 3H-2-Benzazepine, 8-chloro-1-phenyl-, 2-oxide

HRID 464934Notes

Reaction equation

HRID 464934 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH:6]=[CH:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[CH:6]=[CH:7][CH2:8][N+:9]([O-:27])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 132717578-Chloro-1-phenyl-3H-2-benzazepine

Product 1

HCID 30672803H-2-Benzazepine, 8-chloro-1-phenyl-, 2-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10.7 g (42 mmole) of 8-chloro-1-phenyl-3H-2-benzazepine, 10.7 g (53 mmole) of 85% metachloroperbenzoic acid and 100 ml of methylene chloride was stirred at room temperature or 16 hr. The mixture was washed with cold dilute aqueous sodium hydroxide and brine. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was crystallized with ether to give crude product, mp 130°-131° C. Recrystallization from ether gave tan prisms, mp 122°-123° C.

Workup

  1. washThe mixture was washed with cold dilute aqueous sodium hydroxide and brine
  2. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure to dryness
  4. customThe residue was crystallized with ether
  5. customto give crude product, mp 130°-131° C
  6. customRecrystallization from ether
  7. customgave tan prisms, mp 122°-123° C.

Sources & evidence

ORD record
ord-dc72e6edbd0c4346bee3237ec65e4a77
Source dataset
uspto-grants-1985_10
Patent number
US04549988

Reaction notes

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