m-Chloroperbenzoic acid → 1-[5-(2,4-Dichlorophenyl)sulfonyl-4-nitro-2-thienyl]ethanone

HRID 1192065Notes

Reaction equation

HRID 1192065 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([C:11]1[S:15][C:14]([C:16](=[O:18])[CH3:17])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20])=[O:10].ClC1C=C(C=CC=1)C(OO)=[O:27]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([C:11]1[S:15][C:14]([C:16](=[O:18])[CH3:17])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20])(=[O:27])=[O:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 469322451-[5-(2,4-Dichlorophenyl)sulfinyl-4-nitro-2-thienyl]ethanone

Product 1

HCID 469323241-[5-(2,4-Dichlorophenyl)sulfonyl-4-nitro-2-thienyl]ethanoneYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[5-(2,4-dichlorophenyl)sulfinyl-4-nitro-2-thienyl]ethanone (100 mg, 0.275 mmol) in dichloromethane (2 mL), m-chloroperoxybenzoic acid (95 mg, 0.55 mmol) was added slowly at 0° C. The mixture was stirred at ambient temperature for 10 hours. Then the mixture was diluted with dichloromethane (10 mL) and washed with aqueous sodium bicarbonate solution (5 mL×3), then water (5 mL×2) and brine (5 mL). The organic phase was dried (Na2SO4), concentrated under vacuum and the residue was purified by chromatography to afford the title product (75 mg, 72% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.62 (1H, s), 8.32 (1H, d), 8.0 (1H, s), 7.87 (1H, m), 2.67 (3H, s). MS m/z: 378.1 [M+H]+.

Workup

  1. washwashed with aqueous sodium bicarbonate solution (5 mL×3)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated under vacuum
  4. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-0fccb88aa3a84dc087f588994852d28c
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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