4-(Dimethylamino)Benzaldehyde → HCID 54263008, compound

HRID 1762383Notes

Reaction equation

HRID 1762383 reaction equation
Cl.[NH2:2][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH3:8].[CH3:9][N:10]([CH3:19])[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1>C(O)(=O)C>[CH3:9][N:10]([CH3:19])[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[N:2][N:3]2[CH:7]=[CH:6][N:5]=[C:4]2[CH3:8])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 22167428HCID 22167428, compound

Product 1

HCID 54263008HCID 54263008, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.3 g (10 mmol) of 1-amino-2-methylimidazole hydrochloride and 2.2 g (15 mmol) of p-dimethylaminobenzaldehyde are stirred at room temperature in 100 ml of glacial acetic acid for 16 hours. The mixture is evaporated, whereupon the residue is treated four times with ethanol and evaporated each time. The crystalline residue is washed with ether and then treated with saturated sodium hydrogen carbonate solution. The mixture is extracted with methylene chloride, the extract is dried over sodium sulphate, evaporated and the material obtained is recrystallized from methylene chloride/petroleum ether. There is obtained 1-[[p-(dimethylamino)benzylidene]amino]-2-methylimidazole of melting point 166°-167°.

Workup

  1. customThe mixture is evaporated, whereupon the residue
  2. additionis treated four times with ethanol
  3. customevaporated each time
  4. washThe crystalline residue is washed with ether
  5. additiontreated with saturated sodium hydrogen carbonate solution
  6. extractionThe mixture is extracted with methylene chloride
  7. dry with materialthe extract is dried over sodium sulphate
  8. customevaporated
  9. customthe material obtained
  10. customis recrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-f8bfb97ff0c542649c3383c13da24040
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

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