m-Chloroperbenzoic acid → HCID 19607804, compound

HRID 1603157Notes

Reaction equation

HRID 1603157 reaction equation
[S:1]1[CH2:6][CH2:5][N:4]([C:7]([CH2:9][O:10][CH:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C:22](=[O:39])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[CH:25][CH:24]=3)[CH2:14][CH2:13][CH2:12]2)=[O:8])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:48])C=1.S([O-])(O)=O.[Na+]>ClCCl>[O:48]=[S:1]1[CH2:6][CH2:5][N:4]([C:7]([CH2:9][O:10][CH:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[N:15]([C:22](=[O:39])[C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:38])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[CH3:37])=[CH:25][CH:24]=3)[CH2:14][CH2:13][CH2:12]2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 19607984HCID 19607984, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 19607804HCID 19607804, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-8 °C

Procedure

To a solution of 5-(thiomorpholinocarbonylmethoxy)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.40 g) in dichloromethane (40 ml) is added 80% m-chloroperbenzoic acid (175 mg) with stirring at -8° C., and the mixture is stirred at -8° C. for 1 hour. To the reaction solution is added 20% aqueous sodium hydrogensulfite solution (40 ml) and the mixture is stirred at room temperature for 30 minutes. The dichloromethane layer is collected, washed with saturated saline solution and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1) to give 5-[(1-oxothiomorpholino)carbonylmethoxy]-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.32 g) as colorless amorphous.

Workup

  1. stirringthe mixture is stirred at -8° C. for 1 hour
  2. stirringthe mixture is stirred at room temperature for 30 minutes
  3. customThe dichloromethane layer is collected
  4. washwashed with saturated saline solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-7f346463f4ac4865a53e5a692b89842e
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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