m-Chloroperbenzoic acid → N-(2,4-dimethylphenyl)-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide

HRID 1487041Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH2:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11].ClC1C=C(C=CC=1)C(OO)=[O:30]>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:20][O:30]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-(2,4-dimethylphenyl)-N-isobutyl-4-vinylbenzenesulfonamide (1.27 g, 3.70 mmol) in dichloromethane (DCM) (30 mL) stirred under nitrogen at 0° C., was added meta-chloroperoxybenzoic acid (mCPBA) (2.55 g, 14.79 mmol), portionwise. The reaction mixture was stirred at 0° C. for 30 minutes. The reaction was then stirred for 16 hours at 20° C. DCM (20 mL) was added to the mixture. The organic phase was washed with 0.1M sodium hydroxide solution (2×50 mL), dried using a hydrophobic frit and evaporated in vacuo to give the crude product. The sample was loaded in dichloromethane and purified on silica (Si) using a 0-50% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product, 935 mg, as an off-white oil which solidified on standing. LCMS [LCMS1] Rt 1.35 min, m/z (ES+) 360 (M+H).

Workup

stirringThe reaction was then stirred for 16 hours at 20° C
washThe organic phase was washed with 0.1M sodium hydroxide solution (2×50 mL)
customdried
customevaporated in vacuo
customto give the crude product
custompurified on silica (Si)
customevaporated in vacuo

Sources & evidence

ORD record: ord-8832a5c0f27c4baa98cec6fbc01fb987
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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