Imidazole → 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-(1-imidazolyl)phenyl)-1H-imidazole

HRID 1599430Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:12]2[CH:17]=[C:16](F)[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[C:10]=1[CH3:11])=[O:5])[CH3:2].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:12]2[CH:17]=[C:16]([N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-fluorophenyl)-1H-imidazole (20.0 g, 68 mmol), imidazole (4.7 g, 69 mmol), potassium carbonate (9.5 g, 69 mmol) and acetonitrile (150 ml) was stirred at 80° C. for 16 h. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate and washed twice with water. The organic phase was dried (MgSO4), filtered and evaporated in vacuo to give 14.1 g (61%) of 4-ethoxycarbonyl-5-methyl-1-(2-nitro-5-(1-imidazolyl) phenyl)-1H-imidazole.

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue dissolved in ethyl acetate
washwashed twice with water
dry with materialThe organic phase was dried (MgSO4)
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-7d2148cafa414b69ad250edd81a981e0
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741785

Reaction notes

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