Water → HCID 13933710, compound

HRID 2232180Notes

Reaction equation

HRID 2232180 reaction equation
N1C=CC=CC=1.[Cl:7][CH:8]([Cl:12])[C:9](Cl)=[O:10].[NH2:13][C:14]1[N:18]([C:19]2[C:24]([F:25])=[C:23]([F:26])[C:22]([C:27]([F:30])([F:29])[F:28])=[C:21]([F:31])[C:20]=2[F:32])[N:17]=[CH:16][CH:15]=1.O>C(#N)C.C(Cl)Cl>[Cl:7][CH:8]([Cl:12])[C:9]([NH:13][C:14]1[N:18]([C:19]2[C:24]([F:25])=[C:23]([F:26])[C:22]([C:27]([F:30])([F:29])[F:28])=[C:21]([F:31])[C:20]=2[F:32])[N:17]=[CH:16][CH:15]=1)=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6593Dichloroacetyl chlorideHCID 139337095-Amino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)pyrazole

Product 1

HCID 13933710HCID 13933710, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

1.8 ml (0.022 mol) of anhydrous pyridine and 2.1 ml (0.021 mol) of 98 percent pure dichloroacetyl chloride are added in succession to a solution of 6 g (0.02 mol) of 5-amino-1-(2,3,5,6-tetrafluoro-4-trifluoromethylphenyl)-pyrazole in 35 ml of anhydrous acetonitrile. The temperature rises to 35° C. The mixture is subsequently stirred for four hours and then poured onto 150 ml of water. The oily precipitate is taken up in 50 ml of methylene chloride, the aqueous phase is separated off and the organic phase is washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution in succession, dried over magnesium sulphate and freed from the solvent in vacuo. 7.0 g (85% of theory) of 5-dichloroacetamido-1-(2,3,5,6-tetrafluoro-4-trifluoromethyl-phenyl)-pyrazole of melting point 112° C.-114° C. are obtained.

Workup

  1. customrises to 35° C
  2. customthe aqueous phase is separated off
  3. washthe organic phase is washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution in succession
  4. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-f2dabe2dec8240259bea1f16aa4c4489
Source dataset
uspto-grants-1988_11
Patent number
US04787930

Reaction notes

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