HCID 11615419, compound → HCID 70351320, compound

HRID 1762382Notes

Reaction equation

HRID 1762382 reaction equation
[Cl-:1].[NH2:2][N+:3]1[CH:7]=[CH:6][N:5]([NH2:8])[C:4]=1[CH3:9].[CH3:10][N:11]([CH3:24])[C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH:16]=O)=[CH:14][C:13]=1[O:22][CH3:23]>C(O)(=O)C>[Cl-:1].[CH3:10][N:11]([CH3:24])[C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH:16]=[N:2][N+:3]2[CH:7]=[CH:6][N:5]([N:8]=[CH:16][C:15]3[CH:18]=[C:19]([O:20][CH3:21])[C:12]([N:11]([CH3:10])[CH3:24])=[C:13]([O:22][CH3:23])[CH:14]=3)[C:4]=2[CH3:9])=[CH:14][C:13]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 11615419HCID 11615419, compoundHCID 17802501HCID 17802501, compound

Product 1

HCID 70351320HCID 70351320, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.2 g of 1,3-diamino-2-methylimidazolium chloride and 6.9 g of 4-dimethylamino-3,5-dimethoxy-benzaldehyde are dissolved in 100 ml of glacial acetic acid, whereupon the solution is stirred at room temperature for 48 hours. The glacial acetic acid is distilled off in vacuo and the residue is dissolved in 100 ml of ethyl acetate. After crystallization sets in a further 300 ml of ethyl acetate are added thereto, whereupon the mixture is cooled to 10°. The crystallized-out material is filtered off under suction, washed with 100 ml of ethyl acetate and dried over potassium hydroxide in vacuo at 80°. There is obtained 1,3-bis[[4-(dimethylamino)-3,5-dimethoxybenzylidene]amino]-2-methylimidazolium chloride of decomposition point 226°.

Workup

  1. distillationThe glacial acetic acid is distilled off in vacuo
  2. dissolutionthe residue is dissolved in 100 ml of ethyl acetate
  3. customAfter crystallization sets in a further 300 ml of ethyl acetate
  4. additionare added
  5. temperaturewhereupon the mixture is cooled to 10°
  6. filtrationThe crystallized-out material is filtered off under suction
  7. washwashed with 100 ml of ethyl acetate
  8. dry with materialdried over potassium hydroxide in vacuo at 80°

Sources & evidence

ORD record
ord-270f18388799452884964881ecc69e3d
Source dataset
uspto-grants-1989_05
Patent number
US04831151

Reaction notes

Loading…