Dimethylamine → HCID 21516410, compound
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].[H-].[Na+].[Br:30][CH2:31][CH2:32][C:33](Cl)=[O:34].[CH3:36][NH:37][CH3:38]>CCOCC>[BrH:30].[CH3:36][N:37]([CH:32]([CH3:31])[C:33]([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:34])[CH3:38]Participants
6
Procedure
A solution of 10.0 g. (0.026 mol.) of 1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene and 1.8 g. of sodium hydride in 750 ml. of ether is added to a solution of 4.45 g. (0.026 mol.) of 3-bromopropionyl chloride in 50 ml. of ether. The reaction mixture is stirred for 12 hours at 25°, then filtered to remove the precipitate formed during the reaction. The filtrate is cooled to -10° and dimethylamine (0.026 mol.) is added. The mixture is cooled for 12 hours, concentrated in vacuo and the residue is washed with ether-hexane and dried in vacuo to give 3-[2-(N,N-dimethylamino)propionyl]-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene hydrobromide.
Workup
- filtrationfiltered
- customto remove the precipitate
- customformed during the reaction
- temperatureThe filtrate is cooled to -10°
- temperatureThe mixture is cooled for 12 hours
- concentrationconcentrated in vacuo
- washthe residue is washed with ether-hexane
- customdried in vacuo
Sources & evidence
- ORD record
- ord-d6401f8919384849972cdabe17536dfc
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03976633
Reaction notes
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