Methyl Isocyanate → 3-(N-methylcarbamoyl)-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene

HRID 1283792Notes

Reaction equation

HRID 1283792 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[N:17]=[N:18][NH:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=1[C:30]#[N:31])#[N:6]>CCOCC>[CH3:1][NH:2][C:3]([N:17]([C:8]1[CH:9]=[C:10]([C:13]([F:14])([F:15])[F:16])[CH:11]=[CH:12][C:7]=1[C:5]#[N:6])[N:18]=[N:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=1[C:30]#[N:31])=[O:4]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 30354951,3-Bis(2-cyano-5-(trifluoromethyl)phenyl)triazene

Product 1

HCID 215164133-(N-methylcarbamoyl)-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.38 g. (6.7 mmol.) of methyl isocyanate in 20 ml. of ether is added dropwise to 1.6 g. (4.2 mmol.) of 1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene in 125 ml. of ether. The reaction mixture is stirred at 25° for 12 hours, refluxed for 6 hours, then left to stand at 25° for 48 hours. Removal of the solvent under reduced pressure gives 3-(N-methylcarbamoyl)-1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene, m.p. 170° (dec.).

Workup

  1. temperaturerefluxed for 6 hours
  2. waitleft
  3. waitto stand at 25° for 48 hours
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-cd433dff4e784f8abdb06d4196a7f450
Source dataset
uspto-grants-1976_08
Patent number
US03976633

Reaction notes

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