Nitric Acid → Nitric acid--1-[3-(2,4-dichlorophenyl)-3-methyloxiran-2-yl]-1H-imidazole (1/1)

HRID 1577526Notes

Reaction equation

HRID 1577526 reaction equation
[O:1]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=2[Cl:12])([CH3:4])[CH:2]1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.[N+:18]([O-:21])([OH:20])=[O:19]>CCOCC>[N+:18]([O-:21])([OH:20])=[O:19].[O:1]1[C:3]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=2[Cl:12])([CH3:4])[CH:2]1[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 3061545HCID 3061545, compound

Product 1

HCID 3061544Nitric acid--1-[3-(2,4-dichlorophenyl)-3-methyloxiran-2-yl]-1H-imidazole (1/1)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of tri-n-butyltin imidazole (9.28 g), 2-chloro-2-(2,4-dichlorophenyl)propionaldehyde (4.75 g) and toluene (100 ml) was heated under reflux for 5 hours. After cooling, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate and evaporated to remove the solvent. The oily residue was purified by chromatography over silica gel to give 1-[1,2-epoxy-2-(2,4-dichlorophenyl)propyl]imidazole (2.35 g, yield 43.7%) as an oil. The product was dissolved in ether, and the ether solution was neutralized by adding fuming nitric acid to give crystals of 1-[1,2-epoxy-2-(2,4-dichlorophenyl)propyl]-imidazole nitrate, which were recrystallized from methanol.

Sources & evidence

ORD record
ord-d710e3e66a8f4335b8e325ae5143cc34
Source dataset
uspto-grants-1981_09
Patent number
US04288448

Reaction notes

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