Sodium Hydroxide → 5-(p-Chlorophenyl)-4-[(trifluoromethyl)thio]pyrrole-2-carboxylic acid

HRID 129634Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]([O:15]C)=[O:14])=[CH:10][C:9]=2[S:17][C:18]([F:21])([F:20])[F:19])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][C:9]=2[S:17][C:18]([F:20])([F:19])[F:21])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 5-(p-chlorophenyl)-4-[(trifluoromethyl)thio]pyrrole-2-carboxylate (4.89 g, 0.0146 mol) and sodium hydroxide (1.75 g, 0.0437 mol) in a 2:1 methanol/water solution (150 mL) is warmed to 60° C., stirred for three hours, cooled to room temperature with stirring overnight and concentrated in vacuo to remove most of the methanol. The resulting aqueous solution is treated with 10% hydrochloric acid and a white precipitate forms. Ethyl acetate is added and the organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as an off-white solid (4.98 g, mp 176°-178° C.) which is identified by 1HNMR spectral analysis.

Workup

temperaturecooled to room temperature
stirringwith stirring overnight
concentrationconcentrated in vacuo
customto remove most of the methanol
additionThe resulting aqueous solution is treated with 10% hydrochloric acid
additionEthyl acetate is added
customthe organic phase is separated
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e196a6596d5541a7ad20af3a5fa7985e
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05468877

Reaction notes

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