Novoldiamine → 1,3-Bis[[p-(dimethylamino) benzylidene]amino]-2-[[4-(diethylamino)-1-methylbutyl]amino]imidazolium tetrafluoroborate

HRID 1194422Notes

Reaction equation

HRID 1194422 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.[NH2:35][CH:36]([CH2:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH3:37]>C(#N)C>[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]=2[NH:35][CH:36]([CH3:37])[CH2:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 78953NovoldiamineHCID 738675261,3-Bis[[p-(dimethylamino)benzylidene]amino]-2-(methylthio)imidazolium tetrafluoroborate

Product 1

HCID 737710081,3-Bis[[p-(dimethylamino) benzylidene]amino]-2-[[4-(diethylamino)-1-methylbutyl]amino]imidazolium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.47 g of 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-(methylthio)imidazolium tetrafluoroborate are suspended in 50 ml of absolute acetonitrile, whereupon the suspension is treated with 7.8 g of absolute 2-amino-5-(diethylamino)pentane. The mixture is stirred at room temperature under an argon atmosphere for about 24 hours. The insoluble constituents are removed by filtration and the filtrate is treated with 450 ml of diethyl ether. The pale yellow precipitate obtained is removed by filtration under suction, washed three times with diethyl ether and recrystallized from methanol/diethyl ether. There is obtained pale yellow 1,3-bis[[p-(dimethylamino)benzylidene]amino]-2-[[4-(diethylamino)-1-methylbutyl]amino]imidazolium tetrafluoroborate of melting point 187°-191° (decomposition).

Workup

  1. customThe insoluble constituents are removed by filtration
  2. additionthe filtrate is treated with 450 ml of diethyl ether
  3. customThe pale yellow precipitate obtained
  4. customis removed by filtration under suction
  5. washwashed three times with diethyl ether
  6. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-5652f9f406d544c8849dbed3c40d1771
Source dataset
uspto-grants-1989_03
Patent number
US04814332

Reaction notes

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