Phosphorus oxychloride → 2-(1-Methyl-1H-pyrazol-5-yl)-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole

HRID 238374Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]1[C:11]([C:12]([NH:14][NH:15][C:16](=[O:27])[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=O)=[CH:10][CH:9]=[N:8]1>C(#N)C>[CH3:6][N:7]1[C:11]([C:12]2[O:27][C:16]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=3)=[N:15][N:14]=2)=[CH:10][CH:9]=[N:8]1

Participants

Conditions

Temperature: 90 °C

Procedure

Phosphorus oxychloride (1.80 mL) was added to an acetonitrile (4.8 mL) suspension of 1-methyl-N′-[4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-carbohydrazide (300 mg) at a room temperature, and the obtained solution was then heated to reflux at 90° C. for 15 hours. Thereafter, the reaction solution was concentrated under a reduced pressure. A saturated sodium carbonate aqueous solution was added to the residue to convert it to a basic solution, and the resulting solution was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration, so as to obtain the title compound (230 mg) in the form of a brown solid.

Workup

temperaturethe obtained solution was then heated
concentrationThereafter, the reaction solution was concentrated under a reduced pressure
additionA saturated sodium carbonate aqueous solution was added to the residue
extractionthe resulting solution was then extracted with ethyl acetate
washThe organic layer was washed with a saturated saline
dry with materialwas then dried over anhydrous magnesium sulfate
concentrationfollowed by vacuum concentration

Sources & evidence

ORD record: ord-666a2e489bbf45ba8bb39f1ebde6a3a4
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642626B2

Reaction notes

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