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

HRID 2233550Notes

Reaction equation

[CH2:1]([C:5]1[N:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[S:8][C:9]=1[CH2:10][C:11]#N)[CH2:2][CH2:3][CH3:4].[OH-:23].[Na+].Cl.[OH2:26]>C(O)(C)C>[CH2:1]([C:5]1[N:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[S:8][C:9]=1[CH2:10][C:11]([OH:26])=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

1.1 g [4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetonitrile were dissolved in a mixture of 1 ml water and 6 ml isopropanol. 1.36 g Sodium hydroxide were added and the mixture heated to 100° C. After three hours the cooled reaction mixture was neutralized with concentrated hydrochloric acid and extracted three times with portions of 50 ml ethyl acetate. The combined organic extracts were dried over MgSO4 and the solvent was removed in vacuo to provide 1.15 g crude [4-Butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid as brown oil. This material was used without purification.

Workup

customAfter three hours the cooled reaction mixture
extractionextracted three times with portions of 50 ml ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-5c8709fbd9ad4ec39553b36cd73733d2
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709509B2

Reaction notes

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