Pyridine → HCID 13561853, compound

HRID 414335Notes

Reaction equation

HRID 414335 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].N1C=CC=CC=1.[NH2:12][C:13]1[N:17]([C:18]2[C:23]([Cl:24])=[CH:22][C:21]([S:25][C:26]([F:29])([F:28])[F:27])=[CH:20][C:19]=2[Cl:30])[N:16]=[CH:15][C:14]=1[C:31]#[N:32]>C(Cl)(Cl)Cl>[C:1]([NH:12][C:13]1[N:17]([C:18]2[C:23]([Cl:24])=[CH:22][C:21]([S:25][C:26]([F:27])([F:28])[F:29])=[CH:20][C:19]=2[Cl:30])[N:16]=[CH:15][C:14]=1[C:31]#[N:32])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 13561832HCID 13561832, compound

Product 1

HCID 13561853HCID 13561853, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

First 10 ml (0.11 mole) of propionyl chloride and then 1.8 ml (0.02 mole) of pyridine in 15 ml of chloroform are added to a suspension of 3.5 g (0.01 mole) of 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylthio-phenyl)-pyrazole in 30 ml of chloroform at 0° C., with stirring. A clear solution is obtained, and, when the addition has ended, stirring is continued at room temperature for 20 hours. The solution thus obtained is evaporated to dryness. For working up, the residue is taken up in 50 ml of ethanol, aqueous ammonia is added until the reaction is alkaline, the mixture is heated under reflux for 10 minutes, the volatile constituents are removed in vacuo, the residue is taken up in 100 ml of chloroform, the mixture is washed with water, then with 2N aqueous hydrochloric acid and again with water and dried over sodium sulphate and the solvent is removed in vacuo. 3.4 g (83% of theory) of 5-propionylamino-4-cyano-1-(2,6-dichloro-4-trifluoromethylthio-phenyl)-pyrazole of melting point 153° C. to 156° C. are obtained.

Workup

  1. customA clear solution is obtained
  2. additionwhen the addition
  3. stirringstirring
  4. customThe solution thus obtained
  5. customis evaporated to dryness
  6. additionaqueous ammonia is added until the reaction
  7. temperaturethe mixture is heated
  8. temperatureunder reflux for 10 minutes
  9. customthe volatile constituents are removed in vacuo
  10. washthe mixture is washed with water
  11. dry with materialwith 2N aqueous hydrochloric acid and again with water and dried over sodium sulphate
  12. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-9c256efc87c34095a3dbd2d53343a001
Source dataset
uspto-grants-1988_12
Patent number
US04791212

Reaction notes

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