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

HRID 1165384Notes

Reaction equation

HRID 1165384 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]

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 6344DichloromethaneSolvent2×

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-4e9421d0d595467693530ac50d7ee5e5
Source dataset
uspto-grants-1990_03
Patent number
US04909832

Reaction notes

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