4-Nitrobenzylamine → Ethyl 5-(4-fluorophenyl)-2-(4-nitrophenyl)imidazole-4-carboxylate

HRID 1595348Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9](=[N:15]O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:26][C:25]([C:24]3[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:28][CH:27]=3)=[N:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 291474-Nitrobenzylamine

HCID 178472897HCID 178472897, compound

Product 1

HCID 178470207Ethyl 5-(4-fluorophenyl)-2-(4-nitrophenyl)imidazole-4-carboxylateYield 24.3%

Procedure

Ethyl 3-(4-fluorophenyl)-2-hydroxyimino-3-oxopropionate (33.5 g) and 4-nitrobenzylamine (23.7 g) were reacted and treated in the same manner as in Starting Material Synthetic Example 1 to give ethyl 5-(4-fluorophenyl)-2-(4-nitrophenyl)imidazole-4-carboxylate (12.1 g),whichwasdissolvedinethylalcohol. 1MSodiumhydroxidesolution was added and the mixture was reacted and treated in the same manner as in.Starting Material Synthetic Example 2 to give 5-(4-fluorophenyl)-2-(4-nitrophenyl)imidazole-4-carboxylic acid (10.3 g), melting point 173-178° C. (decomposition).

Workup

additiontreated in the same manner as

Sources & evidence

ORD record: ord-89c65ca8fed0485d8ed01b63900ae1d4
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

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