4-(Dimethylamino)Benzaldehyde → HCID 70391578, compound

HRID 1762388Notes

Reaction equation

HRID 1762388 reaction equation
[Cl-].[NH2:2][N+:3]1[CH:7]=[C:6]([CH2:8][Cl:9])[N:5]([NH2:10])[C:4]=1[CH3:11].[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1>C(O)(=O)C>[Cl-:9].[CH3:12][N:13]([CH3:22])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[N:2][N+:3]2[CH:7]=[C:6]([CH2:8][Cl:9])[N:5]([N:10]=[CH:18][C:17]3[CH:20]=[CH:21][C:14]([N:13]([CH3:22])[CH3:12])=[CH:15][CH:16]=3)[C:4]=2[CH3:11])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 70351393HCID 70351393, compound

Product 1

HCID 70391578HCID 70391578, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.985 g (5 mmol) of 1,3-diamino-4-(chloromethyl)-2-methylimidazolium chloride and 7.45 g (50 mmol) of 4-dimethylaminobenzaldehyde are dissolved in 250 ml of glacial acetic acid. The solution is left to stand at room temperature for 36 hours and evaporated. The residue is placed on a column loaded with 150 g of silica gel (particle size 0.063-0.2 mm) and the product is eluted with chloroform/methanol (9:1). The eluate is evaporated and the product is crystallized from ethanol/ether. There is obtained 1,3-bis[[p-(dimethylamino)benzylidene]amino]-4-(chloromethyl)-2-methylimidazolium chloride of melting point 188° (dec.)

Workup

  1. waitThe solution is left
  2. customevaporated
  3. washthe product is eluted with chloroform/methanol (9:1)
  4. customThe eluate is evaporated
  5. customthe product is crystallized from ethanol/ether

Sources & evidence

ORD record
ord-8365968355be4bd9b01ce1d8fc9402a4
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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