m-Chloroperbenzoic acid → N-(5-chloro-2-fluorophenyl)-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide

HRID 1487065Notes

Reaction equation

HRID 1487065 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([N:8]([CH2:20][CH:21]([CH3:23])[CH3:22])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:30]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([N:8]([CH2:20][CH:21]([CH3:22])[CH3:23])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:19][O:30]3)=[CH:14][CH:13]=2)(=[O:10])=[O:11])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 89875834N-(5-chloro-2-fluorophenyl)-N-isobutyl-4-vinylbenzenesulfonamide

Product 1

HCID 89875932N-(5-chloro-2-fluorophenyl)-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamideYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(5-chloro-2-fluorophenyl)-N-isobutyl-4-vinylbenzenesulfonamide (824 mg, 2.240 mmol) in dichloromethane (DCM) at 0° C. was added meta-chloroperoxybenzoic acid (mCPBA) (1546 mg, 8.96 mmol) and the reaction mixture stirred for 6 hours from 0° C. to 25° C. The reaction was then washed with water (5 mL), sodium hydroxide solution (2M, 5 mL) and brine (5 mL), then evaporated in vacuo to give the required product (503 mg). LCMS [LCMS2] Rt 1.34 min, m/z (ES+) 384 (M+H).

Workup

  1. washThe reaction was then washed with water (5 mL), sodium hydroxide solution (2M, 5 mL) and brine (5 mL)
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-f34313188d7f4861991348328cfe0027
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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