m-Chloroperbenzoic acid → HCID 59759966, compound

HRID 1693109Notes

Reaction equation

HRID 1693109 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=3[C:13]=2[CH3:22])(=[O:11])=[O:10])=[C:4]([CH2:23][S:24][CH3:25])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:14]=3[C:13]=2[CH3:22])(=[O:11])=[O:10])=[C:4]([CH2:23][S:24]([CH3:25])=[O:34])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59759972HCID 59759972, compound

Product 1

HCID 59759966HCID 59759966, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-fluoro-3-methyl-benzo[b]thiophene-2-sulfonic acid(4-bromo-2-methylsulfanylmethyl-phenyl)-amide (0.46 g) (cf. example 13a) in chloroform (25 ml) was added m-chloroperbenzoic acid 85% (0.272 g). The reaction mixture was stirred at rt for 18 h, concentrated, and the crude residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain the desired compound (0.31 g) as an off-white solid. MS (ISN): 473.9, 476.0 (M−H)−

Workup

  1. concentrationconcentrated
  2. customthe crude residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-e9f8aab4b9ea435dbf6457f8c9f3a4ce
Source dataset
uspto-grants-2012_04
Patent number
US08158655B2

Reaction notes

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