m-Chloroperbenzoic acid → 9-Chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-6-oxide

HRID 464536Notes

Reaction equation

HRID 464536 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[N:21]=[CH:20][N:19]=[CH:18][C:7]=3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[N:21]=[CH:20][N:19]=[CH:18][C:7]=3[CH2:8][N+:9]([O-:32])=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1317369-Chloro-7-(2-chlorophenyl)-5H-pyrimido(5,4-d)(2)benzazepine

Product 1

HCID 132023249-Chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine-6-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6.8 g (20 mmole) of 9-chloro-7-(2-chlorophenyl)-5H-pyrimido[5,4-d][2]benzazepine, 6 g (30 mmole) of 85% m-chloroperbenzoic acid in 200 ml of methylene chloride was stirred at room temperature for 4 hrs. The mixture was washed with an excess of ice cold dilute sodium hydroxide, dried over ahydrous sodium sulfate and filtered over hyflo. The filtrate was concentrated at reduced pressure to dryness. The residue was crystallized from a mixture of methylene chloride and ether to give a crude product, mp 228°-229° C. Recrystallization from a mixture of methylene chloride and ether gave the product, mp 216°-217° C.

Workup

  1. washThe mixture was washed with an excess of ice cold dilute sodium hydroxide
  2. dry with materialdried over ahydrous sodium sulfate
  3. filtrationfiltered over hyflo
  4. concentrationThe filtrate was concentrated at reduced pressure to dryness
  5. customThe residue was crystallized from a mixture of methylene chloride and ether

Sources & evidence

ORD record
ord-dc83f44845914439b70a6833d6688360
Source dataset
uspto-grants-1985_10
Patent number
US04547581

Reaction notes

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