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

HRID 1032057Notes

Reaction equation

HRID 1032057 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 with 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 and twice with cold methanol
  4. customre-precipitated from dimethylformamide/diethyl ether

Sources & evidence

ORD record
ord-517ccd8747a444dbb059c0cbc14f215b
Source dataset
uspto-grants-1990_09
Patent number
US04956470

Reaction notes

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