Potassium Carbonate → 4-nitro-1-{3-(trifluoromethyl)phenyl}-1H-imidazole

HRID 2409858Notes

Reaction equation

[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].I[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.C(OCC)(=O)C.[Cu]I>[N+:1]([C:4]1[N:5]=[CH:6][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[CH:8]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 85 °C

Procedure

Into a 500-mL round bottom flask, was placed a solution of 4-nitro-1H-imidazole (10 g, 88.50 mmol, 1.00 equiv) in DMSO (50 mL), 1-iodo-3-(trifluoromethyl)benzene (24 g, 88.24 mmol, 1.00 equiv), potassium carbonate (25 g, 181.16 mmol, 2.00 equiv), copper(I) iodide (2.5 g, 13.16 mmol, 0.15 equiv), and L-proline (1.53 g, 13.30 mmol, 0.15 equiv). The resulting solution was stirred overnight at 85° C. in an oil bath. The resulting solution was diluted with 1000 mL of ethyl acetate. The solids were filtered out. The filtrate was washed with 2×500 mL of brine, dried over sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:3) to yield 6.7 g (28%) of 4-nitro-1-(3-(trifluoromethyl)phenyl)-1H-imidazole as a pale solid.

Workup

customInto a 500-mL round bottom flask, was placed
filtrationThe solids were filtered out
washThe filtrate was washed with 2×500 mL of brine
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
washeluted with ethyl acetate/petroleum ether (1:3)

Sources & evidence

ORD record: ord-faff16edbb6b4bbdaa0d47312bea2b10
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815910B2

Reaction notes

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