Sulfuric Acid → HCID 90402802, compound

HRID 2200624Notes

Reaction equation

HRID 2200624 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[N:11]([CH3:18])[C:10]=3[N:9]=[C:8]2S)=[CH:4][CH:3]=1.[Cl:22][O-].[Na+].[S:25](=[O:29])(=O)(O)[OH:26]>>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:15]3[C:14](=[O:16])[NH:13][C:12](=[O:17])[N:11]([CH3:18])[C:10]=3[N:9]=[C:8]2[S:25]([Cl:22])(=[O:29])=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 23665760Sodium HypochloriteHCID 178481640HCID 178481640, compound

Product 1

HCID 90402802HCID 90402802, compoundYield 47.6%

Procedure

To a solution of 7-(4-chlorobenzyl)-8-mercapto-3-methyl-1H-purine-2,6(3H,7H)-dione (400 mg, 1.24 mmol) in concentrated sulfuric acid (5 mL) was added aqueous sodium hypochlorite solution (5 mL, 5% active chlorine) dropwise at 0° C. and the mixture was stirred at room temperature for 15 min. The mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give 7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-sulfonyl chloride (230 mg, 47.6% yield) as brown solid, which was directly used immediately without purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f989270a1db249968b282769aa0ffeba
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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