[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine → 2,3-Dioxobutyranilide 3-(2,6-dichloro-4-trifluoromethylphenylhydrazone) 2-oxime
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[NH:13][NH2:14].[N:15](=[C:17]([C:27](=O)[CH3:28])[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[OH:16]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][N:14]=[C:27]([CH3:28])[C:17](=[N:15][OH:16])[C:18]([NH:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:19]Participants
3
Procedure
2,6-Dichloro-4-trifluoromethylphenylhydrazine was reacted with 2,3-dioxobutyranilide 2-oxime, in a similar manner to above to give 2,3-dioxobutyranilide 3-(2,6-dichloro-4-trifluoromethylphenylhydrazone) 2-oxime, m.p. 185°-186°. This was then treated with acetic anhydride in acetic acid to give 2,3-dioxobutyranilide 2-acetyloxime 3-(2,6-dichloro-4-trifluoromethylphenylhydrazone). This was cyclised with caesium carbonate to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-5-methyl-2H-1,2,3-triazole-4-carboxanilide, m.p. 185°-186°.
Sources & evidence
- ORD record
- ord-2d79895c413c4bc089966488d7c27318
- Source dataset
- uspto-grants-1991_11
- Patent number
- US05064844
Reaction notes
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