Pyridine → HCID 13127539, compound

HRID 1462137Notes

Reaction equation

HRID 1462137 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[Cl:18])[N:9]=[CH:8][C:7]=1[C:19]#[N:20].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]([NH:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:12]=2[Cl:18])[N:9]=[CH:8][C:7]=1[C:19]#[N:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 13127512HCID 13127512, compound

Product 1

HCID 13127539HCID 13127539, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Acetyl chloride (34 ml) was added to a stirred suspension of 5-amino-1-(2-chloro-4-methylphenyl)-4-cyanopyrazole (8.0 g) in chloroform (34 ml) at 0° C. A solution of pyridine (5.4 ml) in chloroform (34 ml) was then added to the suspension thus obtained over 10 minutes, with stirring at 0° C. to 2° C. maintained by external cooling. The reaction mixture was then stirred at laboratory temperature for 2.5 hours and the solution thus obtained was evaporated to dryness. The residue was dissolved in ethanol (100 ml) and basified with aqueous ammonia (d: 0.880). The basified solution was heated at reflux for 10 minutes and then evaporated to dryness. The residue was dissolved in dichloromethane (500 ml) and water (500 ml) and the organic layer was separated, washed successively once with water, twice with 2N hydrochloric acid and twice with water, dried over anhydrous magnesium sulphate and evaporated. The colourless solid thus obtained was crystallised from toluene (30 ml) to give 5-acetamido-1-(2-chloro-4-methylphenyl)-4-cyanopyrazole (6.54 g), m.p. 146°-147° C., in the form of colourless crystals.

Workup

  1. customthus obtained over 10 minutes
  2. temperaturemaintained by external cooling
  3. stirringThe reaction mixture was then stirred at laboratory temperature for 2.5 hours
  4. customthe solution thus obtained
  5. customwas evaporated to dryness
  6. dissolutionThe residue was dissolved in ethanol (100 ml)
  7. temperatureThe basified solution was heated
  8. temperatureat reflux for 10 minutes
  9. customevaporated to dryness
  10. dissolutionThe residue was dissolved in dichloromethane (500 ml)
  11. customwater (500 ml) and the organic layer was separated
  12. washwashed successively once with water, twice with 2N hydrochloric acid and twice with water
  13. dry with materialdried over anhydrous magnesium sulphate
  14. customevaporated
  15. customThe colourless solid thus obtained
  16. customwas crystallised from toluene (30 ml)

Sources & evidence

ORD record
ord-df98ac702e764e3a9e032f840cf020f7
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

Loading…