Hydrochloric Acid → [4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid

HRID 1767881Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[S:5][C:6]=1[CH2:7][C:8]#N.[OH-:20].[Na+].[OH2:22].Cl>C(O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[S:5][C:6]=1[CH2:7][C:8]([OH:22])=[O:20]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of [4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetonitrile (8.86 g, 31 mmol), sodium hydroxide (12.5 g, 314 mmol), water (160 ml) and ethanol (160 ml) was stirred vigorously at 100° C. for 2.5 h. The reaction mixture was poured onto crushed ice and aqueous HCl and extracted three times with dichloromethane. The combined extracts were washed with water and brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave 9.5 g (quant.) of the title compound as light yellow solid.

Workup

additionThe reaction mixture was poured
extractionextracted three times with dichloromethane
washThe combined extracts were washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-bb43e20114094220b1245dd341010c87
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235572B2

Reaction notes

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