Hydrochloric Acid → 2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic acid

HRID 918771Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:29]([F:32])([F:31])[F:30])[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([C:24]([O:26]CC)=[O:25])=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].[OH-].[Na+].Cl>O1CCOCC1>[Cl:9][C:6]1[CH:5]=[C:4]([C:10]2([C:29]([F:32])([F:30])[F:31])[CH2:14][CH2:13][N:12]([C:15]3[S:16][C:17]([C:24]([OH:26])=[O:25])=[C:18]([C:20]([F:23])([F:21])[F:22])[N:19]=3)[CH2:11]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[Cl:8]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(tri-fluoromethyl)-1,3-thiazole-5-carboxylate (2.4 g) was added to a mixture solution comprising 1,4-dioxane (40 mL) and an aqueous solution (40 mL) of sodium hydroxide (2.0 g), followed by heating at 80° C. for ten hours. After cooling, the reaction solution was poured over ice water, acidified by adding concentrated hydrochloric acid, and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was evaporated off under reduced pressure to obtain the title compound (2.25 g, 99%).

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record: ord-ff76faddb21e4f22b8c336a6e273fc61
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09271499B2

Reaction notes

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