4-(Dimethylamino)Benzaldehyde → HCID 178437936, compound

HRID 1762362Notes

Reaction equation

HRID 1762362 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]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[C:15]1[CH2:30][CH3:31]>C(O)(=O)C>[Cl-:12].[CH2:30]([C:15]1[N:14]([N:13]=[CH:7][C:6]2[CH:9]=[CH:10][C:3]([N:2]([CH3:11])[CH3:1])=[CH:4][CH:5]=2)[CH:18]=[CH:17][N+:16]=1[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=1)[CH3:31]

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 178437964HCID 178437964, compound

Product 1

HCID 178437936HCID 178437936, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.5 g (3.38 mmol) of p-dimethylaminobenzaldehyde is added to a solution of 1.0 g (3.38 mmol) of 3-amino-1-[[p-(dimethylamino)benzyl]amino]-2-ethylimidazolium chloride in 15 ml of glacial acetic acid, the mixture is stirred at room temperature for 24 hours, the solution is evaporated and the crude product is chromatographed on 60 g of silica gel (particle size 0.063-0.200 mm) while eluting with methylene chloride/methanol (3:1 v/v). After recrystallizing the resulting material from ethanol/ether there is obtained 2-ethyl-1-[[p-(dimethylamino)benzyl]-amino]-3-[[p-(dimethylamino)benzylidene]amino]imidazolium chloride of melting point 201°-202°.

Workup

  1. customthe solution is evaporated
  2. customthe crude product is chromatographed on 60 g of silica gel (particle size 0.063-0.200 mm)
  3. washwhile eluting with methylene chloride/methanol (3:1 v/v)
  4. customAfter recrystallizing the resulting material from ethanol/ether there

Sources & evidence

ORD record
ord-cbecc42839794965807bfcc93b340295
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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