Acetic Acid → 1-(3-Fluoro-5-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic Acid

HRID 1841256Notes

Reaction equation

HRID 1841256 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[CH:13](OCC)(OCC)OCC.[N+:23]([CH2:26]C(OCC)=O)([O-])=O.[C:32]([OH:35])(=[O:34])[CH3:33]>[Fe]>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[CH:13]=[C:33]([C:32]([OH:35])=[O:34])[N:23]=[CH:26]2)[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 27359133-Amino-5-fluorobenzotrifluoride

Product 1

HCID 234450181-(3-Fluoro-5-trifluoromethyl-phenyl)-1H-imidazole-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 234, 3-fluoro-5-trifluoromethylaniline 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 white crystalline solid. Mp. >250° C. (H2O/dioxane), MS: m/e=273 (M−H−).

Sources & evidence

ORD record
ord-76e6ca90c25e4971bc2063800ecdd890
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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