Water → HCID 178482755, compound

HRID 1032051Notes

Reaction equation

HRID 1032051 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][N:7]([CH3:23])[C:8]1[CH:22]=[CH:21][C:11]([CH:12]=[N:13][N+:14]2[CH:18]=[CH:17][N:16]([CH3:19])[C:15]=2[CH3:20])=[CH:10][CH:9]=1.[CH3:24][N:25]([CH3:34])[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1.N1CCCCC1.O>C1(C)C=CC=CC=1>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:23][N:7]([CH3:6])[C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[N:13][N+:14]2[CH:18]=[CH:17][N:16]([CH3:19])[C:15]=2[CH:20]=[CH:30][C:29]2[CH:32]=[CH:33][C:26]([N:25]([CH3:34])[CH3:24])=[CH:27][CH:28]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74794-(Dimethylamino)BenzaldehydeHCID 8082Piperidine2×HCID 178432783HCID 178432783, compound

Product 1

HCID 178482755HCID 178482755, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.66 g of 1-[[p-(dimethylamino)benzylidene]-amino]-2,3-dimethylimidazolium tetrafluoroborate, 0.45 g of p-(dimethylamino)benzaldehyde and 0.34 g of piperidine are suspended in 30 ml of toluene, whereupon the suspension is heated to boiling under reflux for about 70 hours on a water separator filled with toluene which contains 5% piperidine. The precipitated material is removed by filtration under suction, washed with toluene, twice with diethyl ether and twice with water and recrystallized from methanol. There is obtained colorless 1-[[p-(dimethylamino)benzylidene]amino]-2-[p-(dimethylamino)styryl]-3-methylimidazolium tetrafluoroborate of melting point 235°-238°.

Workup

  1. temperatureis heated
  2. customThe precipitated material is removed by filtration under suction
  3. washwashed with toluene, twice with diethyl ether and twice with water
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4bb37db2b7da41ec89c117a3712e22e0
Source dataset
uspto-grants-1990_09
Patent number
US04956470

Reaction notes

Loading…