p-Nitroacetophenone → HCID 86743048, compound

HRID 1762389Notes

Reaction equation

HRID 1762389 reaction equation
[Cl-:1].[NH2:2][N+:3]1[CH:7]=[CH:6][N:5]([NH2:8])[C:4]=1[CH2:9][CH3:10].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20](=O)[CH3:21])=[CH:16][CH:15]=1)([O-:13])=[O:12]>C(O)(=O)C>[Cl-:1].[NH2:2][N+:3]1[CH:7]=[CH:6][N:5]([N:8]=[C:20]([CH3:21])[C:17]2[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:19][CH:18]=2)[C:4]=1[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 7487p-NitroacetophenoneHCID 70352008HCID 70352008, compound

Product 1

HCID 86743048HCID 86743048, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.24 g (20 mmol) of 1,3-diamino-2-ethylimidazolium chloride and 16.5 g (100 mmol) of p-nitroacetophenone in 150 ml of glacial acetic acid is left to stand for 2 days, concentrated and the residue is crystallized from ethanol/ether. The crystals are placed on a column loaded with 50 g of silica gel. The material eluted with methylene chloride/methanol (7:3) is recrystallized from ethanol. There is obtained 1-amino-2-ethyl-3-[(α-methyl-p-nitrobenzylidene)amino]-imidazolium chloride of melting point 201°-203°.

Workup

  1. concentrationconcentrated
  2. customthe residue is crystallized from ethanol/ether
  3. washThe material eluted with methylene chloride/methanol (7:3)
  4. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-4c089e9dbafa4fd9ac40fe39234bb89e
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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