5-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester → 1-(5-methoxycarbonyl-4-nitro-2-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic acid methyl ester

HRID 2069288Notes

Reaction equation

HRID 2069288 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].[CH3:19][O:20][C:21]([C:23]1[N:24]=[CH:25][NH:26][CH:27]=1)=[O:22]>O1CCCC1.CS(C)=O>[CH3:19][O:20][C:21]([C:23]1[N:24]=[CH:25][N:26]([C:8]2[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:18])[C:5]([N+:15]([O-:17])=[O:16])=[CH:6][C:7]=2[C:11]([F:14])([F:13])[F:12])[CH:27]=1)=[O:22]

Participants

5

Reactant 2

HCID 589644905-Fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl esterHCID 178418785HCID 178418785, compound

Product 1

HCID 589644761-(5-methoxycarbonyl-4-nitro-2-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic acid methyl esterYield 80.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (1 g, 3.74 mmol) and 1H-imidazole-4-carboxylic acid methyl ester (0.53 g, 4.12 mmol) in 10 ml of tetrahydrofuran and 2 ml of DMSO is heated to reflux for 90 hours. The solution is allowed to 5 cool to room temperature and evaporated. The residue is crystallized from dichloromethane and hexane to give 1.12 g (3 mmol, 80%) of 1-(5-methoxycarbonyl-4-nitro-2-trifluoromethyl-phenyl) -1H-imidazole-4-carboxylic acid methyl ester, m.p. 136 -138° C., ES-MS: m/z 374 [M+H]+.

Workup

  1. temperatureto reflux for 90 hours
  2. customevaporated
  3. customThe residue is crystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-e207c9a9b8fe425288c52feec689a383
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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