Hydrogen Peroxide → 3-cyano-6-methyl-5-[4-(methylsulfonyl)phenyl]-2(1H)-pyridinone

HRID 462698

Reaktionsgleichung

Reaktionsgleichung von HRID 462698
[C:1]([C:3]1[C:4](=[O:19])[NH:5][C:6]([CH3:18])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])=[O:16])=[CH:11][CH:10]=2)[CH:8]=1)#[N:2].[OH:20]O>C(O)(=O)C.O[W](O)(=O)=O>[C:1]([C:3]1[C:4](=[O:19])[NH:5][C:6]([CH3:18])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:17])(=[O:20])=[O:16])=[CH:11][CH:10]=2)[CH:8]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 784Hydrogen Peroxide2×HCID 134577123-cyano-6-methyl-5-[4-(methylsulfinyl)phenyl]-2(1H)-pyridinone

Produkt 1

HCID 134577143-cyano-6-methyl-5-[4-(methylsulfonyl)phenyl]-2(1H)-pyridinoneAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1152Tungstic acidKatalysatorHCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

The above 4-(methylsulfonyl)phenyl compound also was prepared from the corresponding 4-(methylsulfinyl)phenyl compound as follows: to a stirred warm solution containing 0.8 g of 3-cyano-6-methyl-5-[4-(methylsulfinyl)phenyl]-2(1H)-pyridinone in 30 ml of glacial acetic acid was added 500 ml tungstic acid and to the resulting stirred solution was added dropwise over a period of 2 minutes a solution containing 0.102 g of hydrogen peroxide in acetic acid (32.97 mg/ml/3.1 ml) and the resulting reaction mixture was stirred at room temperature for 1 hour and then heated occasionally over a period of 1 hour. After tlc analysis indicated a small quantity of methylsulfinyl compound still present, and additional 3 ml of said hydrogen peroxide solution was added and heating as above was continued for 1 hour. The hot reaction mixture was filtered thru diatomaceous earth to remove the tungstic acid, the filter pad washed with warm acetic acid and the filtrate stripped, first in vacuo and then under high vacuum. The remaining solid residue was slurried in about 75 ml of hot absolute ethanol and the mixture cooled slightly. The solid was collected, washed with ethanol and dried at 65° C. in vacuo to yield 0.7 g of 3-cyano-6-methyl-5-[4-(methylsulfonyl)phenyl]-2(1H)-pyridinone, m.p. 311°-313° C.

Aufarbeitung

  1. temperatureto a stirred warm solution
  2. additionwas added dropwise over a period of 2 minutes a solution
  3. customthe resulting reaction mixture
  4. stirringwas stirred at room temperature for 1 hour
  5. temperatureheated occasionally over a period of 1 hour
  6. temperatureheating
  7. filtrationThe hot reaction mixture was filtered
  8. customto remove the tungstic acid
  9. washthe filter pad washed with warm acetic acid
  10. temperaturethe mixture cooled slightly
  11. customThe solid was collected
  12. washwashed with ethanol
  13. customdried at 65° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7709e46c9e2148208328c0119f05ffb3
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04517192

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