Imidazole → HCID 59333299, compound

HRID 1893476Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Br:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene (16.0 g, 0.0556 mol), imidazole (4.0 g, 0.0588 mol) and N,N-diisopropylethylamine (10.1 mL, 0.0582 mol) in acetonitrile (160 mL) is stirred under nitrogen for 1.5 hour at 80° C. After concentration of the reaction mixture, the residue is partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate, the combined organic phases are washed in turn with a saturated solution of ammonium chloride, brine and dried over sodium sulfate. Concentration and purification by cake filtration over silica gel, eluting with a mixture of ethyl acetate and cyclohexane from 2/8 to 1/1 affords the title compound as a yellow solid (16.1 g, 86.2%)

Workup

customAfter concentration of the reaction mixture, the residue is partitioned between water and ethyl acetate
extractionThe aqueous phase is extracted with ethyl acetate
washthe combined organic phases are washed in turn with a saturated solution of ammonium chloride, brine
dry with materialdried over sodium sulfate
concentrationConcentration and purification
filtrationby cake filtration over silica gel
washeluting with a mixture of ethyl acetate and cyclohexane from 2/8 to 1/1

Sources & evidence

ORD record: ord-4242963cda404db48465ed51562c1e37
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513250B2

Reaction notes

Loading…