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

HRID 433620
Notes
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Reaction equation

HRID 433620 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]
ParticipantsProcedureSources & evidenceReaction notes

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 23925
Iron
Catalyst

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-eefacf6657dd4aaa964d55ca05586d76
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06667335B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes