3-Nitrobenzylamine → Ethyl 5-(4-methoxyphenyl)-2-(3-nitrophenyl)imidazole-4-carboxylate

HRID 1595360Notes

Reaction equation

HRID 1595360 reaction equation
O[N:2]=[C:3]([C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][NH2:26])([O-:21])=[O:20]>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[NH:26][C:25]([C:24]3[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=3)=[N:2][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 1227223-NitrobenzylamineHCID 178472900HCID 178472900, compound

Product 1

HCID 178470188Ethyl 5-(4-methoxyphenyl)-2-(3-nitrophenyl)imidazole-4-carboxylateYield 45.5%

Procedure

Ethyl 2-hydroxyimino-3-(4-methoxyphenyl)-3-oxopropionate (20.0 g) and 3-nitrobenzylamine (15.0 g) were reacted and treated in the same manner as in Starting Material Synthetic Example 10 to give ethyl 5-(4-methoxyphenyl)-2-(3-nitrophenyl)imidazole-4-carboxylate (13.3 g), melting point 208-210° C.

Workup

  1. additiontreated in the same manner as

Sources & evidence

ORD record
ord-6207b02a828b4dacb96a62bf96f738ab
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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