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

HRID 1032056

Reaction equation

HRID 1032056 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-ec3f271a912c42e2968aad8e48d1cbd2
Source dataset
uspto-grants-1990_09
Patent number
US04956470

Linked notes

Loading…