Sulfuric Acid → HCID 90402802, Verbindung

Reaktionsgleichung

[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

Komponenten

Edukt 3

HCID 1118Sulfuric Acid

HCID 23665760Sodium Hypochlorite

HCID 178481640HCID 178481640, Verbindung

Produkt 1

HCID 90402802HCID 90402802, VerbindungAusbeute 47,6 %

Versuchsvorschrift

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.