Xanthine → 6-Thioxanthine

HRID 377183

Reaktionsgleichung

Reaktionsgleichung von HRID 377183
[NH:1]1[C:10](=O)[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[NH:4][C:2]1=[O:3].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:13].[OH-].[Na+]>N1C=CC=CC=1>[NH:1]1[C:10](=[S:13])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[NH:4][C:2]1=[O:3]

Komponenten

5

Edukt 3

HCID 1188XanthineHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)

Produkt 1

HCID 12681076-ThioxanthineAusbeute 354,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

6.59 g (19 mM) of xanthine and 5.07 g (22.8 mM) of phosphorus pentasulfide were heated under reflux in 102 ml of pyridine for 3 days. At 0° C., 25.1 ml of 2N NaOH were added. The solid was filtered off and washed with pyridine. The solvents were evaporated in vacuo, the residue suspended in water, collected, redissolved in 100 ml of 1N NaOH and 50 ml of isopropanol, treated twice with 0.3 g of charcoal, filtered and neutralized with 5N HCl to pH 7. The isopropanol was removed in vacuo and the solid collected, washed and dried to give 6.80 g (98.7%) of 6-thioxanthine, mp 188-9° C.

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. washwashed with pyridine
  3. customThe solvents were evaporated in vacuo
  4. customcollected
  5. dissolutionredissolved in 100 ml of 1N NaOH
  6. addition50 ml of isopropanol, treated twice with 0.3 g of charcoal
  7. filtrationfiltered
  8. customThe isopropanol was removed in vacuo
  9. customthe solid collected
  10. washwashed
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5134e4564fc9476f8f4b10e279a89db2
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025361

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