Hydrochloric Acid → 2-phenyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylic Acid

HRID 917299Notes

Reaction equation

C([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([F:20])([F:19])[F:18])=[O:5])C.[Li+].[OH-].Cl>C1COCC1>[C:11]1([C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:17]([F:18])([F:19])[F:20])[N:8]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-phenyl-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester (1.6 g, 5.3 mmol) in THF (16 mL) was added 1 N aqueous LiOH (16 mL, 16 mmol). This mixture was brought to reflux and stirred vigorously for 1 h. The mixture was allowed to cool to 25° C. and 1 N aqueous HCl (35 mL, 35 mmol) was added. The mixture was extracted with ethyl acetate (2×50 mL) and the combined organic extracts were washed with saturated aqueous NaCl (1×50 mL), dried over MgSO4 and concentrated in vacuo to give the carboxylic acid as a white solid (1.32 g, 91%).

Workup

temperatureto reflux
extractionThe mixture was extracted with ethyl acetate (2×50 mL)
washthe combined organic extracts were washed with saturated aqueous NaCl (1×50 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-85c5e04fdb554697932bf8f7c1f8b4d9
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273866B2

Reaction notes

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