Water → 5-(1-Methylcyclopropyl)-3-(2,6-dichloro-4-trifluoromethylphenyl)-1,3,4-oxadiazoline-2-one

HRID 893315Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1([CH:7]2[O:11][C:10](=[O:12])[N:9]=[N:8]2)[CH2:6][CH2:5]1.[Cl:13][C:14]1[CH:15]=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:17]=[C:18]([Cl:21])[C:19]=1Cl.O>CN(C)C=O>[CH3:3][C:4]1([C:7]2[O:11][C:10](=[O:12])[N:9]([C:19]3[C:18]([Cl:21])=[CH:17][C:16]([C:22]([F:23])([F:25])[F:24])=[CH:15][C:14]=3[Cl:13])[N:8]=2)[CH2:6][CH2:5]1

Participants

Conditions

Temperature: 80 °C

Procedure

After 44 mg (1.1 mmol) of 60% sodium hydride was added to a solution of 0.14 g (1 mmol) of 5-(1-methylcyclopropyl)-1,3,4-oxadiazolin-2-one in 5 ml of N,N-dimethylformamide at room temperature, the mixture was stirred at the same temperature for 15 minutes. To the mixture was added 0.25 g (1 mmol) of 3,4,5-trichlorobenzotrifluoride followed by heating a 80° C. for 6 hours. After cooling, the mixture was poured into water and extracted with ethyl acetate. After drying over magnesium sulfate, the extract was concentrated under reduced pressure to give the crude product. The crude product was subjected to silica gel column chromatography to give 35 mg of 5-(1-methylcyclopropyl)-3-(2,6-dichloro-4-trifluoromethylphenyl)-1,3,4-oxadiazoline-2-one.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialAfter drying over magnesium sulfate
concentrationthe extract was concentrated under reduced pressure
customto give the crude product

Sources & evidence

ORD record: ord-646aa1cb31a44cad8eb2bc0d5cde10eb
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05124341

Reaction notes

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