Sodium Hydroxide → 3,9-Dihydro-1H-purine-2,6-dithione

HRID 377181Notes

Reaction equation

HRID 377181 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=[S: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=[S:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 12681852-Thioxanthine

Product 1

HCID 12682523,9-Dihydro-1H-purine-2,6-dithioneYield 258.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

13.22 g (50 mM) of 2-thioxanthine and 13.34 g (60 mM) of phosphorus pentasulfide were heated under reflux in 160 ml of pyridine for 3 days. At 5-10° C., 66 ml (132 mM) of 2N NaOH were added. The solvents were evaporated in vacuo, the residue treated with 200 ml of water and evaporated again. The residue was again suspended in 200 ml of water and collected. The crude product was dissolved in 120 ml of 1N NaOH, treated twice with 0.14 g of charcoal, filtered and acidified with 32 ml of 5N HCl to pH 4.5. The solid was collected, washed and dried to give 14.31 g of crude dithioxanthine. This was dissolved in 300 ml of chloroform; some insoluble material was filtered off, and the solution passed through 71.5 g of silica gel in a column. Crystallization from isopropanol gave 12.17 g (86.8%) of 2,6-dithioxanthine with mp 196-200° C.

Workup

  1. customThe solvents were evaporated in vacuo
  2. additionthe residue treated with 200 ml of water
  3. customevaporated again
  4. customcollected
  5. dissolutionThe crude product was dissolved in 120 ml of 1N NaOH
  6. additiontreated twice with 0.14 g of charcoal
  7. filtrationfiltered
  8. customThe solid was collected
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-b7f0b4f3b75f479998118be4e8adff08
Source dataset
uspto-grants-2000_02
Patent number
US06025361

Reaction notes

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