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

HRID 47107Notes

Reaction equation

HRID 47107 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]=[CH:21][C:20]([S:23][CH3:24])=[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.[OH:28]O>C(O)(=O)C.O.N>[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]=[CH:21][C:20]([S:23]([CH3:24])=[O:28])=[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 2

HCID 784Hydrogen Peroxide2×HCID 706101497,7-dimethyl-2-(2-methoxy-4-methylmercapto-phenyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione

Product 1

HCID 706108267,7-Dimethyl-2-(2-methoxy-4-methylsulfinyl-phenyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

5.1 gm of 7,7-dimethyl-2-(2-methoxy-4-methylmercapto-phenyl)-5H,7H-imidazo[4,5-h]isoquinoline-4,6-dione were reacted in 100 ml of 70% acetic acid with 1.7 gm of 30% hydrogen peroxide, and the mixture was allowed to stand for 50 hours at room temperature (the first 3 hours while stirring). After 18 and again after 26 hours 1.3 gm of 30% hydrogen peroxide were added. The reaction mixture was then diluted with water, and ammonia was added until alkaline reaction. The precipitate was suction-filtered off and the filtrate was extracted twice with chloroform. The combined chloroform phases were evaporated, and the evaporation residue was combined with the precipitate. The thus obtained product was purified on a silicagel column (eluant: chloroform/acetone 19:1).

Workup

  1. additionwas added until alkaline reaction
  2. filtrationThe precipitate was suction-filtered off
  3. extractionthe filtrate was extracted twice with chloroform
  4. customThe combined chloroform phases were evaporated
  5. customThe thus obtained product was purified on a silicagel column (eluant: chloroform/acetone 19:1)

Sources & evidence

ORD record
ord-6e2f49757df540dbb47a68a6ced2992a
Source dataset
uspto-grants-1979_11
Patent number
US04176184

Reaction notes

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