Imidazole → 1-(3-(1-Imidazolyl)-phenyl)-5 trifluoromethyl benzimidazole

HRID 2379124Notes

Reaction equation

HRID 2379124 reaction equation
I[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>CCOCC.O>[N:21]1([C:2]2[CH:3]=[C:4]([N:8]3[C:12]4[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:11]=4[N:10]=[CH:9]3)[CH:5]=[CH:6][CH:7]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 18957889HCID 18957889, compound

Product 1

HCID 194259611-(3-(1-Imidazolyl)-phenyl)-5 trifluoromethyl benzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1-(3-iodophenyl)-5-trifluoromethyl-benzimidazole (2a)(1.0 g, 2.58 mmol), imidazole (0.19 g, 2.73 mmol), potassium carbonate (0.38 g, 2.78 mmol), CuBr (20 mg, 0.15 mmol), and 1-methyl-2-pyrrolidone was heated to 200° C. for 18 hours. Dilution with water and extractive workup with ether was followed by chromatography on silica gel. Yield: 0.43 g, 1.51 mmol, 51%. mp 177°-180° C.

Sources & evidence

ORD record
ord-39ed3c7cda894e5a9a1b3d2f61b5cee2
Source dataset
uspto-grants-1994_11
Patent number
US05360809

Reaction notes

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