Xanthine → 6-Thioxanthine

HRID 1600830Notes

Reaction equation

HRID 1600830 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 12681076-ThioxanthineYield 354.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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 iso-propanol, 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.

Workup

  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 iso-propanol, 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

Sources & evidence

ORD record
ord-9d1a21785faa459f92ce020e195c51f0
Source dataset
uspto-grants-1999_11
Patent number
US05977119

Reaction notes

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