m-Chloroperbenzoic acid → HCID 14500551, compound

HRID 1762863Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1.ClC1C=C(C=CC=1)C(OO)=[O:25]>C(Cl)(Cl)Cl>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10](=[O:19])[C:11]1[CH:12]=[CH:13][C:14]([S:17]([CH3:18])=[O:25])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Ten grams of N-(2,6-dimethylphenyl)-4-(methylthio)benzamide were dissolved in a small volume of chloroform and chilled to 0° C. A solution of 7.9 g of m-chloroperoxybenzoic acid in chloroform was added in dropwise fashion. The reaction was stirred at room temperature for 1 hour, washed with a sodium bicarbonate solution, water, and a saturated chloride solution, dried over sodium sulfate and evaporated in vacuo. The resulting foam was chromatographed over silica gel eluting with an ethyl acetate in hexane gradient. The appropriate fractions were combined and the solvent removed in vacuo and the resulting residue was crystallized from ethyl acetate/hexane providing the desired title product in 59% yield, m.p. 144°-146° C.

Workup

washwashed with a sodium bicarbonate solution, water
dry with materiala saturated chloride solution, dried over sodium sulfate
customevaporated in vacuo
customThe resulting foam was chromatographed over silica gel eluting with an ethyl acetate in hexane gradient
customthe solvent removed in vacuo
customthe resulting residue was crystallized from ethyl acetate/hexane providing the desired title product in 59% yield, m.p. 144°-146° C.

Sources & evidence

ORD record: ord-71e858205fc348beaab5c1343edb7f02
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04835181

Reaction notes

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