Hydrogen Peroxide → 2-(p-Chlorophenyl)-5-[(trifluoromethyl)sulfonyl]pyrrole-3-carbonitrile

HRID 1464681Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.OO.C(OCC)(=[O:24])C.[OH2:28]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:15]([C:16]([F:17])([F:19])[F:18])(=[O:24])=[O:28])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carbonitrile (0.6 g, 0.002 mol) in acetic acid is treated portionwise with 30% hydrogen peroxide solution (0.6 mL, 0.006 mol), stirred for 11/2 hours at 90° C., treated with additional hydrogen peroxide (0.3 mL, 0.003 mol), stirred for two hours at 90° C., stirred for 16 hours at room temperature and diluted with an ethyl acetate/water mixture. The organic phase is separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. The solid is recrystallized from ethylene dichloride to give the title product as a beige solid (mp 228°-230° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

stirringstirred for two hours at 90° C.
stirringstirred for 16 hours at room temperature
customThe organic phase is separated
washwashed with water and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto obtain a solid
customThe solid is recrystallized from ethylene dichloride

Sources & evidence

ORD record: ord-0bcd65f21ddb4882a3ccbae64c79c386
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306827

Reaction notes

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