Acetic Acid → 1-(3-Difluoromethyl-4-fluoro-phenyl)-1H-imidazole-4-carboxylic Acid

HRID 1841251Notes

Reaction equation

HRID 1841251 reaction equation
[F:1][CH:2]([F:11])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[F:10])[NH2:6].[CH:12](OCC)(OCC)OCC.[N+:22]([CH2:25]C(OCC)=O)([O-])=O.[C:31]([OH:34])(=[O:33])[CH3:32]>[Fe]>[F:11][CH:2]([F:1])[C:3]1[CH:4]=[C:5]([N:6]2[CH:12]=[C:32]([C:31]([OH:34])=[O:33])[N:22]=[CH:25]2)[CH:7]=[CH:8][C:9]=1[F:10]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 234450763-(Difluoromethyl)-4-fluoroaniline

Product 1

HCID 234451291-(3-Difluoromethyl-4-fluoro-phenyl)-1H-imidazole-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 234, 3-difluoromethyl-4-fluoroaniline was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The title compound was obtained as a light brown crystalline solid. Mp. >247° C. dec. (H2O/dioxane), MS: m/e=255 (M−H−).

Sources & evidence

ORD record
ord-65067c504dce485e9d4ba35ee2148fc4
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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