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

HRID 973676노트

반응식

HRID 973676 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-c31edd0bb716474ba2a50c1673e3bdf9
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064844

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