1,3-Bis(2-cyano-5-(trifluoromethyl)phenyl)triazene → 3-[4-(N,N-diethylamino)butyryl]-1,3-bis(2-cyano-5-trifluoromethylphenyl)-triazene hydrochloride
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[N:13]=[N:14][NH:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[C:26]#[N:27])#[N:2].[ClH:28].[CH2:29]([N:31]([CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][C:35](O)=[O:36])[CH3:30]>C(Cl)Cl>[ClH:28].[CH2:29]([N:31]([CH2:32][CH2:33][CH2:34][C:35]([N:13]([C:4]1[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2])[N:14]=[N:15][C:16]1[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[CH:18][C:17]=1[C:26]#[N:27])=[O:36])[CH2:38][CH3:39])[CH3:30]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 10.0 g. (0.026 mol.) of 1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene, 6.0 g. (0.029 mol.) of N,N-dicyclohexylcarbodiimide and 5.1 g. (0.026 mol.) of 4-diethylaminobutyric acid hydrochloride in 800 ml. of methylene chloride is stirred at 25° for 12 hours. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure to give a residue which is washed with ether and recrystallized from benzene to give 3-[4-(N,N-diethylamino)butyryl]-1,3-bis(2-cyano-5-trifluoromethylphenyl)-triazene hydrochloride.
Workup
- filtrationThe reaction mixture is filtered
- concentrationthe filtrate is concentrated under reduced pressure
- customto give a residue which
- washis washed with ether
- customrecrystallized from benzene
Sources & evidence
- ORD record
- ord-8ad6a03a424648158ac1c1c825634134
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03976633
Reaction notes
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