Methanesulfenyl chloride, trifluoro- → Ethyl 4-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole-3-carboxylate

HRID 1464670Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[F:18][C:19]([F:23])([F:22])[S:20]Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][NH:11][C:12]=2[S:20][C:19]([F:23])([F:22])[F:18])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of ethyl 4-(p-chlorophenyl)pyrrole-3-carboxylate (9.0 g, 0.036 mol) in methylene chloride (180 mi) is treated with trifluoromethylsulfenyl chloride (4.9 g, 0.036 mol) with stirring for 45 minutes at -30° C. The reaction mixture is warmed to room temperature and stirred for several hours. Since a TLC shows some starting material present, the reaction mixture is cooled to -30° C., treated with additional trifluoromethylsulfenyl chloride (1.3 g, 0.0095 mol), warmed to room temperature overnight with stirring, washed with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as an off-white solid (12.0 g, mp 161.5°-164.00° C.) which is identified by 1HNMR, 19FNMR and 13CNMR spectral analyses.

Workup

temperatureThe reaction mixture is warmed to room temperature
stirringstirred for several hours
temperaturethe reaction mixture is cooled to -30° C.
temperaturewarmed to room temperature overnight
stirringwith stirring
washwashed with water, saturated sodium hydrogen carbonate solution and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dd9f1e78590346f9a21494eb23d5a77f
Source dataset: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05306827

Reaction notes

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