4-(Dimethylamino)Benzaldehyde → HCID 70351879, compound

HRID 1762360Notes

Reaction equation

HRID 1762360 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[CH2:20][CH3:21]>C(O)(=O)C>[Cl-:12].[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:13][N+:14]2[CH:18]=[CH:17][N:16]([N:19]=[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[CH2:20][CH3:21])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 70352008HCID 70352008, compound

Product 1

HCID 70351879HCID 70351879, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.98 g (20 mmol) of p-dimethylaminobenzaldehyde are added to a solution of 3.24 g (20 mmol) of 1,3-diamino-2-ethylimidazolium chloride in 180 ml of glacial acetic acid. The mixture is stirred at room temperatured for 50 hours, the precipitated 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-ethylimidazolium chloride is then filtered off and washed with ethanol. The mother liquor is evaporated and the residue is placed on a column loaded with 200 g of silica gel (particle size: 0.063-0.200 mm). By elution with methylene chloride/methanol (9:1 v/v) there is obtained a further portion of 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-ethyl-imidazolium chloride.

Workup

  1. filtrationthe precipitated 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-ethylimidazolium chloride is then filtered off
  2. washwashed with ethanol
  3. customThe mother liquor is evaporated
  4. washBy elution with methylene chloride/methanol (9:1 v/v) there

Sources & evidence

ORD record
ord-5251508130174784931787098076fde8
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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