m-Chloroperbenzoic acid → Benzenesulfonamide, 4-hydroxy-N-(2-oxiranylmethyl)-N-(1-phenylethyl)-
Reaction equation
[CH2:1]([N:4]([CH:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[O:31]1[CH2:3][CH:2]1[CH2:1][N:4]([CH:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6]Participants
Procedure
5 ml of chloroform solution containing 1 g (3.2 mmol) of N-allyl-N-α-methylbenzyl-4-hydroxybenzenesulfonamide was added to 30 ml of a chloroform solution of 828 mg (4.8 mmol) of metachloroperbenzoic acid, followed by refluxing for 2 hours. After completion of the reaction, the chloroform solution was washed with an aqueous sodium thiosulfate solution and then an aqueous sodium bicarbonate solution. After drying, the solvent was distilled off and the resulting crude product was purified by the silica gel column chromatography (hexane-ethyl acetate) to obtain 910 mg of N-(2,3-epoxypropyl)-N-α-methylbenzyl-4-hydroxybenzenesulfonamide (Compound No. 37). The melting point was found to be 82.0° to 86.0° C. The results of the elemental analysis are shown below.
Workup
- temperatureby refluxing for 2 hours
- customAfter completion of the reaction
- washthe chloroform solution was washed with an aqueous sodium thiosulfate solution
- customAfter drying
- distillationthe solvent was distilled off
- customthe resulting crude product was purified by the silica gel column chromatography (hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-404183832eed4948a32c40a3b053ed95
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04468245
Reaction notes
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