m-Chloroperbenzoic acid → HCID 19607898, compound

HRID 745084Notes

Reaction equation

HRID 745084 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([N:13]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH:17]=[CH:16][CH2:15][CH2:14]2)=[O:12])=[CH:9][CH:8]=1)=[O:5].ClC1C=CC=C(C(OO)=[O:38])C=1>ClCCl>[O:38]1[CH:17]2[CH:16]1[CH2:15][CH2:14][N:13]([C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=3[Cl:1])=[CH:25][CH:24]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=12

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19608163HCID 19608163, compound

Product 1

HCID 19607898HCID 19607898, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[4-(2-Chlorobenzoylamino)benzoyl]-2,3-dihydro-1H-benzazepine (4.7 g) is dissolved in dichloromethane (50 ml) and thereto is added 80% m-chloroperbenzoic acid (3 g). The mixture is stirred at room temperature overnight. The dichloromethane layer is washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated saline solution, and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1) to give 4,5-epoxy-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (4.26 g) as white powder.

Workup

  1. washThe dichloromethane layer is washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated saline solution
  2. distillationthe solvent is distilled off under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-bc04d573f28d4782835376bde8b80e93
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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