Water → HCID 13630542, compound

HRID 65384

Reaction equation

HRID 65384 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[N:10]=[CH:9][C:8]=1[N:24]1[CH:28]=[N:27][CH:26]=[N:25]1.N1C=CC=CC=1.O>C(#N)C>[Cl:23][C:13]1[CH:14]=[C:15]([C:19]([F:20])([F:22])[F:21])[CH:16]=[C:17]([Cl:18])[C:12]=1[N:11]1[C:7]([NH:6][C:1](=[O:4])[CH2:2][CH3:3])=[C:8]([N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[CH:9]=[N:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 62324Propionyl chlorideHCID 136305415-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(1,2,4-triazol-1-yl)-pyrazole

Product 1

HCID 13630542HCID 13630542, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

3.5 g (0.037 mole) of propionyl chloride are added dropwise to a solution of 7.3 g (0.02 mole) of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(1,2,4-triazol-1-yl)-pyrazole and 2 g (0.025 mole) of pyridine in 60 ml of acetonitrile, with stirring, and, when the addition has ended, the mixture is stirred at room temperature for a further 12 to 15 hours. For working up, the reaction batch is poured into water and extracted with methylene chloride, the organic phase is washed with water and dried over sodium sulphate and the solvent is removed in vacuo. The residue is dissolved in 100 ml of ethanol, 10 ml of aqueous ammonia are added, the mixture is heated to 50° C. for 15 minutes and concentrated in vacuo and the residue is triturated with water and dried on clay. 6.8 g (81% of theory) of 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-propionylamino-4-(1,2,4-triazol-1-yl)-pyrazole of melting point 167° C. to 169° C. are obtained.

Workup

  1. additionwhen the addition
  2. stirringthe mixture is stirred at room temperature for a further 12 to 15 hours
  3. extractionextracted with methylene chloride
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is removed in vacuo
  7. dissolutionThe residue is dissolved in 100 ml of ethanol
  8. addition10 ml of aqueous ammonia are added
  9. concentrationconcentrated in vacuo
  10. customthe residue is triturated with water
  11. customdried on clay

Sources & evidence

ORD record
ord-1b6cce64a360415b9921215c57a9826e
Source dataset
uspto-grants-1986_09
Patent number
US04614534

Linked notes

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