p-Toluenesulfonic acid → 4-(1,3,4-oxadiazol-2-yl)benzoic Acid

HRID 1093772

Reaction equation

[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[NH:12]([C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)=[O:15])[NH2:13].C(OC(OCC)OCC)C>O>[O:15]1[CH:1]=[N:13][N:12]=[C:14]1[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Hydrazine hydrate was added to a solution of terephthalic acid monomethyl ester (1 g, 5.5 mmol) in MeOH (10 mL) and stirring was continued for 1 hr. The reaction mixture was concentrated to afford 900 mg (90.09% Yield) of 4-hydrazinocarbonyl-benzoic acid. p-Toluene sulfonic acid (48 mg, 0.277 mmol) was added to a solution of 4-hydrazinocarbonyl-benzoic acid (500 mg, 2.77 mmol) in triethylorthoformate (7.5 mL, 44.0 mmol) and stirring was continued with heating at 100° C. for 3 hrs. The reaction mixture was diluted with water, the solid was collected to afford 200 mg (37.9% Yield) of 4-[1,3,4]oxadiazol-2-yl-benzoic acid.

Workup

customthe solid was collected

Sources & evidence

ORD record: ord-bf4112086728446eb8be8ccc85d693be
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129376B2

Linked notes

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