Diisopropylethylamine → 5-(4-Cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

HRID 2069294Notes

Reaction equation

HRID 2069294 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8](F)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[NH:19]1[CH:23]=[C:22]([C:24]#[N:25])[N:21]=[CH:20]1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:19]2[CH:23]=[C:22]([C:24]#[N:25])[N:21]=[CH:20]2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl esterHCID 178510437HCID 178510437, compound

Product 1

HCID 589644895-(4-Cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl esterYield 8.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (3.2 g, 11.98 mmol), 1H-imidazole-4-carbonitrile (2.017 g, 14.37 mmol) and ethyl-diisopropyl-amine (8.4 ml, 47.9 mmol) in 10 ml of dioxane is heated to reflux for 24 hours. The solution is allowed to cool to room temperature and evaporated. The residue is chromatographed on silica gel using gradients of dichloromethane and methanol to give 0.36 g (1.05 mmol, 8.8%) of amorphous 5-(4-cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester, ES-MS: m/z 341 [M+H]+.

Workup

  1. temperatureto reflux for 24 hours
  2. customevaporated
  3. customThe residue is chromatographed on silica gel using gradients of dichloromethane and methanol

Sources & evidence

ORD record
ord-af8ae5bd93dc4527a00024f382ef69cb
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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