Toluene → 3-[(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazol-4-yl]-2-propenal

HRID 1031157Notes

Reaction equation

HRID 1031157 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16](C=O)[CH:15]=[N:14]1.C(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:21].[C:42]1([CH3:48])C=CC=C[CH:43]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16]([CH:43]=[CH:42][CH:48]=[O:21])[CH:15]=[N:14]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 197783082-(2,6-Dichloro-4-trifluoromethylphenyl)-1,2,3-triazole-4-carboxaldehyde

Product 1

HCID 867457303-[(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazol-4-yl]-2-propenal

Procedure

2-(2,6-Dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-carboxaldehyde (2 g) and formylmethylene triphenylphosphorane (1.9 g) were heated under reflux in toluene for 4 hours. After removal of the solvent at reduced pressure the resulting residue was purified by column chromatography to give 3-[(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazol-4-yl]-2-propenal, m.p. 68°-69°. This compound (1.8 g) was then stirred with diaminomaleonitrile (0.6 g) in methanol containing a trace of p-toluenesulphonic acid for 4 hours. Removal of the solvent at reduced pressure and column chromatography gave 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[3-(2-amino-1,2-dicyanoethenylimino)-2-propenyl]-2H-1,2,3-triazole, m.p. 207°-209°.

Workup

  1. customAfter removal of the solvent at reduced pressure the resulting residue
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6aab16d9eb554f38b4d5bdd739644c63
Source dataset
uspto-grants-1992_04
Patent number
US05109012

Reaction notes

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