Diaminomaleonitrile → 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(2-amino-1,2-dicyanoethenylimino)methyl]-1H-1,2,3-triazole
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]([CH:18]=O)[N:15]=[N:14]1.[NH2:20]/[C:21](/[C:26]#[N:27])=[C:22](\[NH2:25])/[C:23]#[N:24]>CO>[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]([CH:18]=[N:20][C:21]([C:26]#[N:27])=[C:22]([NH2:25])[C:23]#[N:24])[N:15]=[N:14]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- waitleft
- customThe solvent was evaporated
- customthe residue was purified by column chromatography and recrystallisation from ethyl acetate/light petroleum (bp 60°-80°)
Sources & evidence
- ORD record
- ord-9daa6745279b48989a6af300289c701b
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05109012
Reaction notes
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