Hydrogen Peroxide → 1,3(2H,4H)-Isoquinolinedione, 4,4-dimethyl-2-(2-(methylsulfinyl)ethyl)-

HRID 1448038Notes

Reaction equation

HRID 1448038 reaction equation
OO.[CH3:3][C:4]1([CH3:20])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[N:6]([CH2:15][CH2:16][S:17][CH3:18])[C:5]1=[O:19].O.C(=O)([O-])[O-:23]>C(O)(=O)C>[CH3:3][C:4]1([CH3:20])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[N:6]([CH2:15][CH2:16][S:17]([CH3:18])=[O:23])[C:5]1=[O:19]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 19660Carbonate IonHCID 30534781,3(2H,4H)-Isoquinolinedione, 4,4-dimethyl-2-(2-(methylthio)ethyl)-

Product 1

HCID 30534791,3(2H,4H)-Isoquinolinedione, 4,4-dimethyl-2-(2-(methylsulfinyl)ethyl)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.9 ml of 30% hydrogen peroxide were added to a solution of 16 gm of 4,4-dimethyl-2-(2-methylmercapto-ethyl)-2H,4H-isoquinoline-1,3-dione in 30 ml of glacial acetic acid, while maintaining the temperature between 20° and 40° C. After 15 minutes the reaction mixture was poured into water, and the resulting mixture was neutralized with ptoassium carbonate and extracted with chloroform. The chloroform phase was evaporated, the residue was purified on a silicagel column (eluant: chloroform/acetone 19:1), and after evaporation of the eluate the residue was recrystallized from cyclohexane by addition of seed crystals.

Workup

  1. temperaturewhile maintaining the temperature between 20° and 40° C
  2. extractionextracted with chloroform
  3. customThe chloroform phase was evaporated
  4. customthe residue was purified on a silicagel column (eluant: chloroform/acetone 19:1)
  5. customafter evaporation of the eluate the residue
  6. customwas recrystallized from cyclohexane by addition of seed crystals

Sources & evidence

ORD record
ord-311dba5dd39d4f40be76976bc9aa7a38
Source dataset
uspto-grants-1979_12
Patent number
US04179508

Reaction notes

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