Water → 5-Cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole

HRID 1194266Notes

Reaction equation

HRID 1194266 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25]([CH2:27][C:28](Cl)=[O:29])#[N:26].O>C(#N)C>[C:25]([CH2:27][C:28]([NH:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[CH:4][CH:3]=1)=[O:29])#[N:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 110515942-Cyanoacetyl chlorideHCID 135571095-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole

Product 1

HCID 139850675-Cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazoleYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

22.5 g (0.076 mol) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole and 8 g (0.1 mol) of pyridine are taken in 200 ml of acetonitrile, and 13.2 g (0.128 mol) of cyanoacetyl chloride are added dropwise at 20°-25° C., while stirring and cooling. The reaction mixture is stirred at room temperature for a further two hours and then poured into water. After extraction with methylene chloride and drying of the organic phase over sodium sulphate, the solvent is distilled off in vacuo. The crystalline residue is stirred with a mixture of ligroin and diisopropyl ether and filtered off with suction. 22 g (80% of theory) of 5-cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of melting point 169°-175° C. are obtained.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture is stirred at room temperature for a further two hours
  3. extractionAfter extraction with methylene chloride
  4. dry with materialdrying of the organic phase over sodium sulphate
  5. distillationthe solvent is distilled off in vacuo
  6. stirringThe crystalline residue is stirred with a mixture of ligroin and diisopropyl ether
  7. filtrationfiltered off with suction

Sources & evidence

ORD record
ord-766122a87d3147c59c59249c7b8aa355
Source dataset
uspto-grants-1989_03
Patent number
US04814001

Reaction notes

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