m-Chloroperbenzoic acid → HCID 13228385, compound

HRID 1388620Notes

Reaction equation

HRID 1388620 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH:14]=[C:13]2[C:7]([CH2:8][N:9]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:11]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:12]=32)=[CH:6]1)=[O:4].ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]([N:5]1[CH:14]=[C:13]2[C:7]([CH2:8][N+:9]([O-:35])=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:11]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:12]=32)=[CH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13067117HCID 13067117, compound

Product 1

HCID 13228385HCID 13228385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4.2 g (11 mmol) of 8-chloro-6-(2-chlorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-carboxylic acid methyl ester and 3.15 g (14.5 mmol) of m-chloroperbenzoic acid in 100 ml of methlene chloride was stirred at 0° for 2.5 hr. The mixture was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was crystallized from ether to give a white solid, mp 224°-226°. Recrystallization from a mixture of ether and methylene chloride gave colorless prisms, mp 226°-227°.

Workup

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated at reduced pressure to dryness
  4. customThe residue was crystallized from ether
  5. customto give a white solid, mp 224°-226°
  6. customRecrystallization
  7. additionfrom a mixture of ether and methylene chloride
  8. customgave colorless prisms, mp 226°-227°

Sources & evidence

ORD record
ord-5bbfbdf66594494ab6061f2d0dcd1f82
Source dataset
uspto-grants-1984_02
Patent number
US04431823

Reaction notes

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