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

HRID 462698

反応式

HRID 462698 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 134577143-cyano-6-methyl-5-[4-(methylsulfonyl)phenyl]-2(1H)-pyridinone収率 82.6%

試薬・触媒・溶媒 2

HCID 1152Tungstic acid触媒HCID 176Acetic Acid溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7709e46c9e2148208328c0119f05ffb3
出典データセット
uspto-grants-1985_05
特許番号
US04517192

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