Carbon Disulfide → HCID 18985861, compound

HRID 2396681Notes

Reaction equation

HRID 2396681 reaction equation
[NH:1]([C:3]1[C:4]2N=CC=C[C:5]=2[N:6]=[C:7]([S:9][CH3:10])[N:8]=1)[NH2:2].[C:15](=[S:17])=S.[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCOCC.C(N(CC)CC)C.O1CCOCC1>[CH2:18]([S:17][C:15]1[N:8]2[C:7]([S:9][CH3:10])=[N:6][C:5]3[N:1]=[CH:3][CH:4]=[CH:5][C:4]=3[C:3]2=[N:1][N:2]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 6348Carbon DisulfideHCID 7503Benzyl Chloride2×HCID 18985860HCID 18985860, compound

Product 1

HCID 18985861HCID 18985861, compoundYield 158.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

4-Hydrazino-2-methylthiopyrido[3,2-d]pyrimidine (14.5 g, 70 mmol) was combined with 200 mL of dioxane, 12.6 mL (16.0 g, 210 mmol) of carbon disulfide, and 29 mL (21.2 g, 210 mmol) of triethylamine and the mixture was heated at reflux with stirring for 4 hours during which time another 50 mL of dioxane was added to facilitate stirring. The mixture was allowed to cool, 13.3 g (105 mmol) of benzyl chloride was added, and the resulting mixture was allowed to stir overnight. Another 6 g of benzyl chloride and 25 mL of triethylamine were added and the mixture was heated to reflux with stirring for a short period. The volatile components were removed by evaporation under reduced pressure and the residue was diluted with dichloromethane and water. The resultant emulsion was filtered to obtain separable phases and the organic phase was washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was diluted with hexane and the resulting black solid was recovered by filtration. This solid was diluted with dichloromethane and the solution obtained was filtered through silica gel. Evaporation of the filtrate under reduced pressure gave a black solid that was diluted with ether and recovered by filtration to obtain 18.8 g the title compound melting at 157°-158° C. The proton NMR spectrum was compatible with the assigned structure. Work up of the filtrate gave an additional 6 g of impure title compound as a black oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. additionwas added
  4. temperatureto cool
  5. stirringto stir overnight
  6. temperaturethe mixture was heated
  7. temperatureto reflux
  8. stirringwith stirring for a short period
  9. customThe volatile components were removed by evaporation under reduced pressure
  10. additionthe residue was diluted with dichloromethane and water
  11. filtrationThe resultant emulsion was filtered
  12. customto obtain separable phases
  13. washthe organic phase was washed with water
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated by evaporation under reduced pressure
  16. additionThe residue was diluted with hexane
  17. filtrationthe resulting black solid was recovered by filtration
  18. additionThis solid was diluted with dichloromethane
  19. customthe solution obtained
  20. filtrationwas filtered through silica gel
  21. customEvaporation of the filtrate under reduced pressure
  22. customgave a black solid
  23. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-65f20f9bb0be4bc7939c8d3813d8d9dd
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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