4-(Dimethylamino)Benzaldehyde → HCID 70360969, compound

HRID 1194415Notes

Reaction equation

HRID 1194415 reaction equation
[Cl-:1].[CH3:2][N:3]([CH3:29])[C:4]1[CH:28]=[CH:27][C:7]([CH:8]=[N:9][N+:10]2[CH:14]=[CH:13][N:12]([N:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[C:11]=2[CH3:26])=[CH:6][CH:5]=1.[CH3:30][N:31]([CH3:40])[C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1.N1CCCCC1>C(O)C>[Cl-:1].[CH3:25][N:23]([CH3:24])[C:20]1[CH:21]=[CH:22][C:17]([CH:16]=[N:15][N+:12]2[CH:13]=[CH:14][N:10]([N:9]=[CH:8][C:7]3[CH:6]=[CH:5][C:4]([N:3]([CH3:2])[CH3:29])=[CH:28][CH:27]=3)[C:11]=2[CH:26]=[CH:36][C:35]2[CH:38]=[CH:39][C:32]([N:31]([CH3:40])[CH3:30])=[CH:33][CH:34]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 8082PiperidineHCID 70351311HCID 70351311, compound

Product 1

HCID 70360969HCID 70360969, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.82 g of 1,3-bis[[p-(dimethylamino)-benzylidene]amino]-2-methylimidazolium chloride is suspended in 30 ml of ethanol, whereupon the suspension is treated with 0.3 g of 4-dimethylaminobenzaldehyde and 0.17 g of piperidine and heated to boiling under reflux. A deep red solution results. After 20 hours it is left to cool. The precipitated product is removed by filtration and re-precipitated from methylene chloride/ether. After recrystallization from toluene there is obtained 1,3-bis[[p-(dimethyl-amino)benzylidene]amino]-2-[p-(dimethylamino)styryl]imidazolium chloride as a red solid of melting point 238°-240°.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customA deep red solution results
  4. temperatureto cool
  5. customThe precipitated product is removed by filtration
  6. customre-precipitated from methylene chloride/ether
  7. customAfter recrystallization from toluene

Sources & evidence

ORD record
ord-54efbafc5083449da4a3c4f8b241bbc2
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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