Sodium Carbonate → HCID 15871256, compound

HRID 1600827Notes

Reaction equation

HRID 1600827 reaction equation
Cl.[NH2:2][C:3]1[C:4](=[O:15])[N:5]([CH2:13][CH3:14])[C:6](=[S:12])[N:7]([CH2:10][CH3:11])[C:8]=1[NH2:9].C(=O)([O-])[O-].[Na+].[Na+].[CH:22]1([C:25](Cl)=O)[CH2:24][CH2:23]1>N1C=CC=CC=1.CCOCC>[CH2:13]([N:5]1[C:4](=[O:15])[C:3]2[NH:2][C:25]([CH:22]3[CH2:24][CH2:23]3)=[N:9][C:8]=2[N:7]([CH2:10][CH3:11])[C:6]1=[S:12])[CH3:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 86754738HCID 86754738, compound

Product 1

HCID 15871256HCID 15871256, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

25.1 g (100 mM) of 5,6-diamino-1,3-diethyl-2-thiouracil HCl were dissolved in 400 ml of pyridine, 12.72 g (120 mM) of sodium carbonate added, and under cooling a solution of 10.77 ml (120 mM) of cyclopropanecarbonyl chloride in 50 ml of dried ether added within 10 min. After 20 min the solvents were evaporated in vacuo. The residue was treated with 200 ml of water and about 50 ml were removed again in vacuo. The suspension was diluted with 100 ml of 2N aqueous sodium hydroxide (NaOH) and heated under reflux for 30 min. A further 80 ml were distilled off during this time. After cooling the solution was acidified with 5N aqueous hydrochloric acid (HCl) to pH 5.5; 200 ml of water was added and the resulting suspension filtered. The solid was collected and washed, redissolved in 200 ml of 1N NaOH, treated twice with 0.4 g of charcoal, filtered and acidified again to pH 4.5. The solid was collected again, washed and dried to give 25.5 g of a solid which was suspended in 400 ml of hot methanol. The solid was collected again, washed and dried to give 23.5 g (89.0%) of 2-thioxanthine with mp subl 265-7° C.

Workup

  1. additionadded within 10 min
  2. customAfter 20 min the solvents were evaporated in vacuo
  3. additionThe residue was treated with 200 ml of water and about 50 ml
  4. customwere removed again in vacuo
  5. additionThe suspension was diluted with 100 ml of 2N aqueous sodium hydroxide (NaOH)
  6. temperatureheated
  7. temperatureunder reflux for 30 min
  8. distillationA further 80 ml were distilled off during this time
  9. temperatureAfter cooling the solution
  10. addition200 ml of water was added
  11. filtrationthe resulting suspension filtered
  12. customThe solid was collected
  13. washwashed
  14. dissolutionredissolved in 200 ml of 1N NaOH
  15. additiontreated twice with 0.4 g of charcoal
  16. filtrationfiltered
  17. customThe solid was collected again
  18. washwashed
  19. customdried

Sources & evidence

ORD record
ord-699138135dd14c70b8b49981eed87ec1
Source dataset
uspto-grants-1999_11
Patent number
US05977119

Reaction notes

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