Ammonia → 2-Amino-1,3-bis[[p-(dimethylamino)benzylidene]amino]imidazolium tetrafluoroborate

HRID 1194423Notes

Reaction equation

HRID 1194423 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][N:7]([CH3:34])[C:8]1[CH:33]=[CH:32][C:11]([CH:12]=[N:13][N+:14]2[CH:18]=[CH:17][N:16]([N:19]=[CH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=3)[C:15]=2SC)=[CH:10][CH:9]=1.[NH3:35].CS.C(OCC)C>CN(C)C=O>[F:1][B-:2]([F:5])([F:4])[F:3].[NH2:35][C:15]1[N:14]([N:13]=[CH:12][C:11]2[CH:32]=[CH:33][C:8]([N:7]([CH3:34])[CH3:6])=[CH:9][CH:10]=2)[CH:18]=[CH:17][N+:16]=1[N:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 878MethanethiolHCID 3283Diethyl EtherHCID 738675261,3-Bis[[p-(dimethylamino)benzylidene]amino]-2-(methylthio)imidazolium tetrafluoroborate

Product 1

HCID 738675312-Amino-1,3-bis[[p-(dimethylamino)benzylidene]amino]imidazolium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.99 g of 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-(methylthio)imidazolium tetrafluoroborate is dissolved in 15 ml of absolute dimethylformamide. Dry ammonia is conducted into the reaction solution at room temperature while stirring until the cleavage of methyl mercaptan is complete. The solution is treated with diethyl ether. The precipitate obtained is washed twice with water and twice and cold methanol and re-precipitated from dimethylformamide/diethyl ether. There is obtained yellow 2-amino-1,3-bis[[p-(dimethylamino)benzylidene]amino]imidazolium tetrafluoroborate with a decomposition point >260°.

Workup

  1. customis conducted into the reaction solution at room temperature
  2. customThe precipitate obtained
  3. washis washed twice with water
  4. customtwice and cold methanol and re-precipitated from dimethylformamide/diethyl ether

Sources & evidence

ORD record
ord-ddbdacf00e8d4edcb9475339aca3359f
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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