Bromomethyl 4-methoxyphenyl ketone → 3-[[p-(Dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)-1-(p-methoxyphenacyl)imidazolium bromide

HRID 1194433Notes

Reaction equation

HRID 1194433 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][Br:9])=[CH:5][CH:4]=1.[CH3:13][N:14]([CH3:36])[C:15]1[CH:35]=[CH:34][C:18]([CH:19]=[N:20][N:21]2[CH:25]=[CH:24][N:23]=[C:22]2[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:17][CH:16]=1>CC(O)C>[Br-:9].[CH3:36][N:14]([CH3:13])[C:15]1[CH:16]=[CH:17][C:18]([CH:19]=[N:20][N:21]2[CH:25]=[CH:24][N+:23]([CH2:8][C:7]([C:6]3[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[O:10])=[C:22]2[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 54562755HCID 54562755, compound

Product 1

HCID 703611883-[[p-(Dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)-1-(p-methoxyphenacyl)imidazolium bromide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.92 g of p-methoxyphenacyl bromide is added to a solution of 0.32 g of 1-[[p-(dimethylamino)-benzylidene]amino]-2-(p-methoxyphenyl)imidazole in 20 ml of 2-propanol. After stirring for 3 days with the exclusion of light, the mixture is evaporated. The residue is placed on a column loaded with 20 g of silica gel. The product is eluted with methylene chloride/methanol (9:1). After crystallization from ethanol/ether, there is obtained 3-[[p-(dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)-1-(p-methoxyphenacyl)imidazolium bromide of melting point 188°-191°.

Workup

  1. customthe mixture is evaporated
  2. washThe product is eluted with methylene chloride/methanol (9:1)
  3. customAfter crystallization from ethanol/ether

Sources & evidence

ORD record
ord-9729e302b16a422983d9ac063f8d31cc
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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