Hydrogen Peroxide → 7,7-Dimethyl-2-(2-methoxy-5-methylsulfinyl-phenyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione

HRID 47111Notes

Reaction equation

HRID 47111 reaction equation
[CH3:1][C:2]1([CH3:27])[C:11](=[O:12])[CH:10]2[C:5](=[C:6]3[N:16]=[C:15]([C:17]4[CH:22]=[C:21]([S:23][CH3:24])[CH:20]=[CH:19][C:18]=4[O:25][CH3:26])[N:14]=[C:7]3[C:8](=[O:13])[CH2:9]2)[CH:4]=[N:3]1.OO.C(=O)([O-])[O-:31].[K+].[K+]>C(O)(=O)C.O>[CH3:1][C:2]1([CH3:27])[C:11](=[O:12])[CH:10]2[C:5](=[C:6]3[N:16]=[C:15]([C:17]4[CH:22]=[C:21]([S:23]([CH3:24])=[O:31])[CH:20]=[CH:19][C:18]=4[O:25][CH3:26])[N:14]=[C:7]3[C:8](=[O:13])[CH2:9]2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 706105377,7-dimethyl-2-(2-methoxy-5-metylmercapto-phenyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione

Product 1

HCID 706112317,7-Dimethyl-2-(2-methoxy-5-methylsulfinyl-phenyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3.0 gm of 7,7-dimethyl-2-(2-methoxy-5-metylmercapto-phenyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione were dissolved in 60 ml of glacial acetic acid and then 0.88 ml of 30% hydrogen peroxide were slowly added dropwise at room temperature. After stirring for 30 minutes, the solution was neutralized with an aqueous saturated potassium carbonate solution, diluted with water and extracted with chloroform. The residual crude product obtained after evaporation of the chloroform was purified on a silicagel column (eluant: chloroform with increasing content of acetone).

Workup

  1. extractionextracted with chloroform

Sources & evidence

ORD record
ord-6eb985a28a664703bc52f315ce989e06
Source dataset
uspto-grants-1979_11
Patent number
US04176184

Reaction notes

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