m-Chloroperbenzoic acid → HCID 13228385, compound

HRID 2296324Notes

Reaction equation

HRID 2296324 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-cd6cb19c53dd4ee3a1e5bafcffbc9f9d
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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