Hydrochloric Acid → 4-{3-[4-(Trifluoromethyl)phenyl]-1,2,4-oxadiazol-5-yl}benzoic acid

HRID 1354448Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)[O:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[F:25][C:2]([F:1])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[O:11][N:10]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 4-[3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-5-yl]benzoate (2.10 g), 1 M aqueous sodium hydroxide solution (12 ml), tetrahydrofuran (20 ml) and methanol (20 ml) was stirred at 60° C. for 1 hr. The mixture was acidified by adding 1 M hydrochloric acid. The crystals were collected by filtration to give 4-[3-(4-trifluoromethylphenyl)-1,2,4-oxadiazol-5-yl]benzoic acid (1.82 g, yield 90%). Recrystallization from hexane-tetrahydrofuran gave colorless crystals. melting point: 293–294° C.

Workup

filtrationThe crystals were collected by filtration

Sources & evidence

ORD record: ord-32792ece49784744a267e4af6e125061
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223791B2

Reaction notes

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