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

HRID 1192064Notes

Reaction equation

HRID 1192064 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[S:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].ClC1C=C(C=CC=1)C(OO)=[O:26]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([C:10]1[S:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19])=[O:26]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 469319521-[5-(2,4-Dichlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone

Product 1

HCID 469322451-[5-(2,4-Dichlorophenyl)sulfinyl-4-nitro-2-thienyl]ethanoneYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[5-(2,4-Dichlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone (200 mg, 0.58 mmol) as prepared in example 2 in dichloromethane (5 mL), m-chloroperoxybenzoic acid (198 mg, 1.14 mmol) was added slowly at 0° C. The mixture was stirred at ambient temperature for 10 hours. After this time the mixture was diluted with dichloromethane (25 mL) and washed with aqueous sodium bicarbonate solution (10 mL×3), then water (10 mL×2) and brine (5 mL). The organic phase was dried (Na2SO4), concentrated under vacuum to afford a yellow solid as the title product (0.14 g, 67% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.65 (1H, s), 7.96 (1H, d), 7.63 (2H, m), 2.66 (3H, s). MS m/z: 362.10 [M+H]+.

Workup

  1. washwashed with aqueous sodium bicarbonate solution (10 mL×3)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-43b6bb9a6e734557a98afbaf87d66de3
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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