Acetyl chloride → 3-Acetyl-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene

HRID 1283789Notes

Reaction equation

HRID 1283789 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+].[C:30](Cl)(=[O:32])[CH3:31]>CCOCC>[C:30]([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:32])[CH3:31]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 30354951,3-Bis(2-cyano-5-(trifluoromethyl)phenyl)triazene

Product 1

HCID 215163803-Acetyl-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5.6 g. (0.015 mol.) of 1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene in 450 ml. of warm ether is added dropwise to a slurry of 1.20 g. (0.025 mol.) of 50% sodium hydride in 15 ml. of ether. Upon cessation of gas evolution, 1.42 g. (0.018 mol.) of acetyl chloride is gradually added and the reaction mixture is stirred for two hours at 25°. The mixture is filtered to remove excess sodium hydride and the filtrate is concentrated to give 3-acetyl-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene, m.p. 111°-112° (hexane).

Workup

  1. filtrationThe mixture is filtered
  2. customto remove excess sodium hydride
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-0798df346f6649fa8ca7dd510fd34f9b
Source dataset
uspto-grants-1976_08
Patent number
US03976633

Reaction notes

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