2-Bromo-1-(4-(dimethylamino)phenyl)ethanone → 3-[p-(Dimethylamino)phenacyl]-1-[[p-(dimethylamino)benzylidene]-amino]-2-ethylimidazolium bromide

HRID 1762374Notes

Reaction equation

HRID 1762374 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:17]=[CH:16][C:6]([CH:7]=[N:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH2:14][CH3:15])=[CH:5][CH:4]=1.[CH3:19][N:20]([CH3:31])[C:21]1[CH:30]=[CH:29][C:24]([C:25](=[O:28])[CH2:26][Br:27])=[CH:23][CH:22]=1>>[Br-:27].[CH3:31][N:20]([CH3:19])[C:21]1[CH:30]=[CH:29][C:24]([C:25](=[O:28])[CH2:26][N:11]2[CH:12]=[CH:13][N+:9]([N:8]=[CH:7][C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:18])=[CH:17][CH:16]=3)=[C:10]2[CH2:14][CH3:15])=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 1422252-Bromo-1-(4-(dimethylamino)phenyl)ethanoneHCID 545500571-[[p-(Dimethylamino)benzylidene]amino]-2-ethylimidazole

Product 1

HCID 1784376873-[p-(Dimethylamino)phenacyl]-1-[[p-(dimethylamino)benzylidene]-amino]-2-ethylimidazolium bromide

Procedure

A solution of 2.42 g (10 mmol) of 1-[[p-(dimethylamino)benzylidene]amino]-2-ethylimidazole is treated with 2.42 g (10 mmol) of p-dimethylaminophenacyl bromide. After stirring at 40° for 30 minutes the product is crystallized out by the addition of ether and recrystallized from methylene chloride/ether. There is obtained 3-[p-(dimethylamino)phenacyl]-1-[[p-(dimethylamino)benzylidene]-amino]-2-ethylimidazolium bromide of melting point 247°.

Workup

  1. customis crystallized out by the addition of ether
  2. customrecrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-3b0badc59d78432386b636b340d5edc9
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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