Dimethylamine → 1,3-Bis[[p-(dimethylamino)benzylidene]amino]-2-(dimethylamino)imidazolium tetrafluoroborate

HRID 1194420Notes

Reaction equation

HRID 1194420 reaction equation
[CH3:1][NH:2][CH3:3].[F:4][B-:5]([F:8])([F:7])[F:6].[CH3:9][N:10]([CH3:37])[C:11]1[CH:36]=[CH:35][C:14]([CH:15]=[N:16][N+:17]2[CH:21]=[CH:20][N:19]([N:22]=[CH:23][C:24]3[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[C:18]=2SC)=[CH:13][CH:12]=1.CN(C)C=O>C(OCC)C>[F:4][B-:5]([F:8])([F:7])[F:6].[CH3:9][N:10]([CH3:37])[C:11]1[CH:36]=[CH:35][C:14]([CH:15]=[N:16][N+:17]2[CH:21]=[CH:20][N:19]([N:22]=[CH:23][C:24]3[CH:29]=[CH:28][C:27]([N:30]([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[C:18]=2[N:2]([CH3:3])[CH3:1])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6228DimethylformamideHCID 738675261,3-Bis[[p-(dimethylamino)benzylidene]amino]-2-(methylthio)imidazolium tetrafluoroborate

Product 1

HCID 738675331,3-Bis[[p-(dimethylamino)benzylidene]amino]-2-(dimethylamino)imidazolium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Gaseous dimethylamine is passed through a mixture of 2.47 g of 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2 (methylthio)imidazolium tetrafluoroborate and 30 ml of absolute dimethylformamide until a weight increase of 0.4 g (corresponding to 1.8 equivalents) is achieved and the mixture is subsequently stirred at room temperature overnight. From the resulting reddish solution, there is obtained by the addition of diethyl ether a crystalline precipitate which is removed by filtration under suction and washed twice with water and ethanol each time. After re-precipitation from dimethylformamide/diethyl ether, there is obtained 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-(dimethylamino)imidazolium tetrafluoroborate as a yellow solid of melting point 248°-252° (decomposition).

Workup

  1. temperatureincrease of 0.4 g (corresponding to 1.8 equivalents)
  2. customis removed by filtration under suction
  3. washwashed twice with water and ethanol each time
  4. customAfter re-precipitation from dimethylformamide/diethyl ether

Sources & evidence

ORD record
ord-afca72476eb84b50b13bee159508e2bc
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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