4-(Dimethylamino)Benzaldehyde → Imidazolium Acetate

HRID 1194430Notes

Reaction equation

HRID 1194430 reaction equation
N[N:2]1[CH:6]=[CH:5][N:4]=[C:3]1C1C=[CH:11][C:10]([O:13]C)=CC=1.CN(C)C1C=CC(C=[O:22])=CC=1>C(O)(=O)C>[C:10]([O-:13])(=[O:22])[CH3:11].[NH+:2]1[CH:6]=[CH:5][NH:4][CH:3]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 221673981-Amino-2-(p-methoxyphenyl)imidazole

Product 1

HCID 66735416Imidazolium Acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9 g of 1-amino-2-(p-methoxyphenyl)imidazole are dissolved in 300 ml of glacial acetic acid, whereupon the solution is treated with 21.3 g of p-(dimethylamino) benzaldehyde. After 24 hours, the mixture is evaporated and the residue is placed on a column loaded with 300 g of silica gel. The product is eluted with dichloro-methane/methanol (95:5). The dark eluate is treated with active carbon and evaporated. The product is crystallized twice from methylene chloride/petroleum ether. There is obtained 1-[[p-(dimethylamino)benzylidene]amino]-2-p-methoxyphenyl)imidazolium acetate of melting point 93°. The resulting salt is treated with aqueous sodium bicarbonate solution and extracted with dichloromethane. The extract is dried over sodium sulfate and evaporated. The product is crystallized from petroleum ether. There is obtained 1-[[p-(dimethylamino)benzylidene]amino]-2-(p-methoxyphenyl)imidazole of melting point 108°.

Workup

  1. customthe mixture is evaporated
  2. washThe product is eluted with dichloro-methane/methanol (95:5)
  3. additionThe dark eluate is treated with active carbon
  4. customevaporated
  5. customThe product is crystallized twice from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-ecfdd46a0122468ea254e39fa4c41da4
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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