Pyridine → 5-(2,4-Dichlorophenoxyacetamido)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole

HRID 569709

Reaction equation

HRID 569709 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:9]=1[O:10][CH2:11][C:12](Cl)=[O:13].[NH2:20][C:21]1[N:25]([C:26]2[C:31]([Cl:32])=[CH:30][C:29]([C:33]([F:36])([F:35])[F:34])=[CH:28][C:27]=2[Cl:37])[N:24]=[CH:23][CH:22]=1>ClCCl>[Cl:7][C:8]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:9]=1[O:10][CH2:11][C:12]([NH:20][C:21]1[N:25]([C:26]2[C:31]([Cl:32])=[CH:30][C:29]([C:33]([F:34])([F:36])[F:35])=[CH:28][C:27]=2[Cl:37])[N:24]=[CH:23][CH:22]=1)=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 69887(2,4-Dichlorophenoxy)acetyl chlorideHCID 135571095-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole

Product 1

HCID 139117395-(2,4-Dichlorophenoxyacetamido)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazoleYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.2 ml (0.0275 mol) of anhydrous pyridine and 6.7 g (0.027 mol) of 96.3 percent strength 2,4-dichlorophenoxyacetyl chloride are added successively to 8 g (0.027 mol) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole (cf. U.S. Pat. No. 4,614,533, supra, in 60 ml of dichloromethane with stirring at 0° C. to 5° C. and the mixture is stirred for 16 hours at room temperature. The mixture is worked up by adding 100 ml of dichloromethane, washing successively with dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution, drying the organic phase over magnesium sulphate and removing the solvent in vacuo. 12.7 g (94.3% of theory) of 5-(2,4-dichlorophenoxyacetamido)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole of melting point 167° C.-180° C. are obtained.

Workup

  1. washwashing successively with dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution
  2. dry with materialdrying the organic phase over magnesium sulphate
  3. customremoving the solvent in vacuo

Sources & evidence

ORD record
ord-55b6c277f7e24b56919f2ba491507085
Source dataset
uspto-grants-1988_03
Patent number
US04734125

Linked notes

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