Reaction #8517

Reaction equation

chloroacetyl chloride

2,6-dichloro-4-trifluoromethylphenylhydrazine

sodium hydroxide

→

title compound

Yield 91.0%

N′-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazide

Yield 91.0%

Solvents

dichloromethane

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Temperaturemaintaining between 5 and 12° C. under an argon atmosphere
2. 2
   Washthe organic phase washed (water)
3. 3
   Dryingdried (magnesium sulfate)
4. 4
   Otherevaporated

Procedure

A solution of chloroacetyl chloride (2.3 ml, 1.08 equivalents) in anhydrous dichloromethane (30 ml) was added during 30 minutes to a stirred solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (6.1 g, 24.89 mmol) in anhydrous dichloromethane (60 ml) maintaining between 5 and 12° C. under an argon atmosphere. The mixture was then stirred for 5-12 hours at 20° C. A solution of sodium hydroxide (11.2 ml of 10%) and dichloromethane were added and the organic phase washed (water), dried (magnesium sulfate) and evaporated to give the title compound (7.25 g) as a white solid, NMR 4.05 (s, 2H), 6.77 (s, 1H), 7.47 (s, 2H), 8.6 (s, 1H). The yield was 91%.

Source