1,4-Dinitro-1H-imidazole → HCID 178526813, compound

HRID 353913Notes

Reaction equation

HRID 353913 reaction equation
[C:1]1([C@@H:7]2[CH2:10][C@H:9]([NH2:11])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](N1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=[CH:16]1)([O-])=O>>[N+:20]([C:18]1[N:17]=[CH:16][N:11]([C@H:9]2[CH2:8][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:10]2)[CH:19]=1)([O-:22])=[O:21]

Participants

3

Reactant 2

HCID 51694961,4-Dinitro-1H-imidazoleHCID 178511727HCID 178511727, compound

Product 1

HCID 178526813HCID 178526813, compoundYield 46%

Procedure

This reaction was carried out using the procedure for Preparation 1 with cis-3-phenylcyclobutylamine (J. Med. Pharm. Chem 1960, 2, 687-691; ACIEE 1981, 20, 879-880) and 1,4-dinitroimidazole to afford 46 mg (46% yield) of 4-nitro-1-(cis-3-phenyl-cyclobutyl)-1H-imidazole; 1H NMR (300 MHz, CDCl3) δ7.9 (s, 1H), 7.55 (s, 1H), 7.4-7.2 (m, 5H), 4.73 (m, 1H), 3.48 (m, 1H), 3.12 (m, 2H), 2.54 (m, 2H); MS (AP/Cl): 244 (M+H)+.

Sources & evidence

ORD record
ord-4ff4dbb85f9641a49ad7096dcdbfbffb
Source dataset
uspto-grants-2004_06
Patent number
US06756385B2

Reaction notes

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