Water → HCID 178482755, compound

HRID 1194417Notes

Reaction equation

HRID 1194417 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-748d988178df41659b59b2b89822a963
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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