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Dichloroacetyl chloride → 5-Dichloroacetamido-1-(2,3,6-trichloro-4-trifluoromethyl-phenyl)-pyrazole

HRID 34859
Notes
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Reaction equation

HRID 34859 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][CH:8]([Cl:12])[C:9](Cl)=[O:10].[NH2:13][C:14]1[N:18]([C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[C:21]([Cl:30])[C:20]=2[Cl:31])[N:17]=[CH:16][CH:15]=1>ClCCl>[Cl:7][CH:8]([Cl:12])[C:9]([NH:13][C:14]1[N:18]([C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:27])[F:28])=[C:21]([Cl:30])[C:20]=2[Cl:31])[N:17]=[CH:16][CH:15]=1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 10340Sodium CarbonateHCID 136896131H-Pyrazol-5-amine, 1-[2,3,6-trichloro-4-(trifluoromethyl)phenyl]-

Product 1

HCID 139134305-Dichloroacetamido-1-(2,3,6-trichloro-4-trifluoromethyl-phenyl)-pyrazoleYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Procedure

15.3 g (0.145 mol) of anhydrous sodium carbonate and 4.76 ml (0.048 mol) of 98% strength dichloroacetyl chloride are added in succession, at 5° C. to 10° C., to 8.0 g (0.024 mol) of 5-amino-1-(2,3,6-trichloro-4-trifluoromethyl-phenyl)-pyrazole in 80 ml of dichloromethane. The mixture is stirred for 4 hours at 5° C.-10° C. and for 13 hours at room temperature. The mixture is diluted with 80 ml of dichloromethane, filtered, and washed in succession with water and saturated sodium chloride solution. The organic phase is dried over magnesium sulphate and freed from the solvent in vacuo. 10.0 g (93.5% of theory) of 5-dichloroacetamido-1-(2,3,6-trichloro-4-trifluoromethyl-phenyl)-pyrazole of melting point 156° C.-161° C. are obtained.

Workup

  1. filtrationfiltered
  2. washwashed in succession with water and saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate

Sources & evidence

ORD record
ord-c3d814524d1c47dabe278a17cca85bd0
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04764202

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes