4-(Dimethylamino)Benzaldehyde → 1,3-Bis[[p-(dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)imidazolium chloride

HRID 1032059Notes

Reaction equation

HRID 1032059 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[Cl-:12].[NH2:13][N+:14]1[CH:18]=[CH:17][N:16]([NH2:19])[C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1>C(O)(=O)C>[Cl-:12].[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:19][N+:16]2[CH:17]=[CH:18][N:14]([N:13]=[CH:7][C:6]3[CH:9]=[CH:10][C:3]([N:2]([CH3:11])[CH3:1])=[CH:4][CH:5]=3)[C:15]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 703609421,3-Diamino-2-(4-methoxyphenyl)imidazolium chloride

Product 1

HCID 703609651,3-Bis[[p-(dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)imidazolium chloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

131 mg of 4-(dimethylamino)benzaldehyde are added to a solution of 90 mg of 1,3-diamino-2-(4-methoxyphenyl) imidazolium chloride in 2 ml of glacial acetic acid. After stirring at room temperature for 48 hours, the dark yellow solution is evaporated. The residue is placed on a column loaded with 8 g of silica gel, whereupon the product is eluted with dichloromethane/ethanol (9:1) and recrystallized from ethanol/ether. There is obtained 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)imidazolium chloride of melting point 250°.

Workup

  1. customthe dark yellow solution is evaporated
  2. washis eluted with dichloromethane/ethanol (9:1)
  3. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-36cddd8c8eb0448c90da541845c2a544
Source dataset
uspto-grants-1990_09
Patent number
US04956470

Reaction notes

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