Methane → HCID 13373119, compound

HRID 257322Notes

Reaction equation

HRID 257322 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][N:8]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].N1C=CC=CC=1.[C:26](Cl)(=[O:28])[CH3:27].C.[CH2:31]([O:33]CC)[CH3:32]>C(Cl)Cl.O>[Cl:13][C:12]1[C:7]([N:6]2[C:2]([N:1]([C:31]([CH3:32])=[O:33])[C:26]([CH3:27])=[O:28])=[C:3]([C:18]#[N:19])[CH:4]=[N:5]2)=[N:8][CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=1

Participants

8

Reactant 5

HCID 297MethaneHCID 1049PyridineHCID 3283Diethyl Ether2×HCID 6367Acetyl chlorideHCID 13373118HCID 13373118, compound

Product 1

HCID 13373119HCID 13373119, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Under a dry nitrogen atmosphere, a stirred mixture of 5.02 grams (0.0175 mole) of 5-amino-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-4-cyanopyrazole and 12.7 grams (0.161 mole) of pyridine in 470 mL of methylene chloride was cooled to 5° C. Acetyl chloride (12.5 grams, 0.159 mole) was added dropwise. After the addition was complete, the reaction mixture was heated at reflux for approximately 20 hours. The mixture was then cooled, treated with decolorizing charcoal, and filtered through a pad of Celite® filter aid. The filtrate was evaporated under reduced pressure, leaving a residue. This residue was stirred vigorously with a mixture of water and diethyl ether. The diethyl ether was allowed to evaporate at room temperature and pressure, leaving an aqueous slurry, which was cooled in an ice bath and then filtered. The filter cake was washed with water and air dried to yield 6.6 grams of 1(3-chloro-5-trifluoromethylpyridin-2-yl)-4-cyano-5-bis(methylcarbonyl)aminopyrazole, m.p. 129.5°-132° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for approximately 20 hours
  4. temperatureThe mixture was then cooled
  5. filtrationfiltered through a pad of Celite®
  6. filtrationfilter aid
  7. customThe filtrate was evaporated under reduced pressure
  8. customleaving a residue
  9. customto evaporate at room temperature
  10. custompressure, leaving an aqueous slurry, which
  11. temperaturewas cooled in an ice bath
  12. filtrationfiltered
  13. washThe filter cake was washed with water and air
  14. customdried

Sources & evidence

ORD record
ord-bd5d740580e14b61a2043dd4f9df5b23
Source dataset
uspto-grants-1993_11
Patent number
US05262382

Reaction notes

Loading…