Water → 2-(2,6-Dichloro-4-trifluoromethylphenylhydrazono)acetaldehyde

HRID 973676ノート

反応式

HRID 973676 の反応式
[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].[CH:15]([CH:17]=O)=[O:16].O>C(O)(=O)C>[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]=[CH:17][CH:15]=[O:16]

参加物

5

反応物 3

HCID 962WaterHCID 7860GlyoxalHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

生成物 1

HCID 867452022-(2,6-Dichloro-4-trifluoromethylphenylhydrazono)acetaldehyde

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (5 g) in acetic acid was added dropwise to a mixture of 40% aqueous glyoxal (50 ml) and water (400 ml). The mixture was stirred at room temperature for 2 hours and solid collected by filtration. A sample was recrystallised from ethanol to give 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)acetaldehyde, m.p. 131°-133°. This crude product (2.85 g) in ethanol (30 ml) was added to a solution of hydroxylamine hydrochloride (0.7 g) in water (10 ml), which had been neutralized with sodium acetate (0.82 g). The mixture was stirred at room temperature and then extracted with ethyl acetate. The extract was washed with brine, dried and evaporated to 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)acetaldehyde oxime. This was then treated with copper sulphate, in a similar manner to Example 1, to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole 1-oxide, m.p. 153°-154°, which in turn was treated with trimethyloxonium tetrafluoroborate and sodium methanethiolate, in a similar manner to Example 3, to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-methylthio-2H-1,2,3-triazole, m p. 100°-101°. (Compound 11)

後処理

  1. filtrationsolid collected by filtration
  2. customA sample was recrystallised from ethanol

出典と根拠

ORDレコード
ord-c31edd0bb716474ba2a50c1673e3bdf9
出典データセット
uspto-grants-1991_11
特許番号
US05064844

反応ノート

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