Chloroacetyl chloride → N'-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazide

HRID 8421

Reaction equation

HRID 8421 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[NH:18][NH2:19].[OH-].[Na+]>ClCCl>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:15])([F:14])[F:16])[CH:10]=[C:9]([Cl:17])[C:8]=1[NH:18][NH:19][C:3](=[O:4])[CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 22015908N'-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

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%.

Workup

  1. temperaturemaintaining between 5 and 12° C. under an argon atmosphere
  2. washthe organic phase washed (water)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-dfa9e18eb14e412c912226bdf971231a
Source dataset
uspto-grants-2006_08
Patent number
US07087786B2

Linked notes

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