HCID 19778386, compound → 1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-1,2,3-triazole-4-carboxaldehyde

HRID 2082383Notes

Reaction equation

HRID 2082383 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[CH:17]=[C:16]([CH2:18][OH:19])[N:15]=[N:14]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[CH:17]=[C:16]([CH:18]=[O:19])[N:15]=[N:14]1

Participants

4

Reactant 1

HCID 19778386HCID 19778386, compound

Product 1

HCID 197783831-(2,6-dichloro-4-trifluoromethylphenyl)-1H-1,2,3-triazole-4-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of this alcohol (1.7 g) and manganese dioxide (6.9 g) in chloroform (40 ml) was stirred at room temperature for 24 hours. This mixture was then filtered through Kieselguhr and the solvent evaporated to give crude material, which was purified by flash column chromatography (silica) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-1H-1,2,3-triazole-4-carboxaldehyde, m.p 143°-144.5°. The aldehyde (2.32 g) and diaminomaleonitrile (0.85 g) were heated under reflux in methanol (40 ml) for 6 hours and then left to stand for 60 hours at room temperature. The solvent was evaporated and the residue was purified by column chromatography and recrystallisation from ethyl acetate/light petroleum (bp. 60°-80°) to give 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(2-amino-1,2-dicyanoethenylimino)methyl]-1H-1,2,3-triazole, m.p.184°-186° (dec.).

Workup

  1. filtrationThis mixture was then filtered through Kieselguhr
  2. customthe solvent evaporated
  3. customto give crude material, which
  4. customwas purified by flash column chromatography (silica)

Sources & evidence

ORD record
ord-af5ea6323b204e019e649b01ece76a1d
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Reaction notes

Loading…