Acetic Acid → HCID 18985862, compound

HRID 2396687Notes

Reaction equation

HRID 2396687 reaction equation
[CH2:1]([S:8][C:9]1[N:13]2[C:14](SC)=[N:15][C:16]3[S:20][CH:19]=[CH:18][C:17]=3[C:12]2=[N:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](OC)(=[O:26])C=C.C[O-].[Na+].C(O)(=O)C>CO.ClCCl>[CH2:1]([S:8][C:9]1[N:13]=[C:12]2[N:11]([C:14]([O:26][CH3:23])=[N:15][C:16]3[S:20][CH:19]=[CH:18][C:17]=32)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7294Methyl AcrylateHCID 10942334Sodium Methoxide3×HCID 18985863HCID 18985863, compound

Product 1

HCID 18985862HCID 18985862, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent4×HCID 6344DichloromethaneSolvent

Procedure

3-Benzylthio-5-methylthiothieno[3,2-e][1,2,4]-triazolo[4,3-c]pyrimidine (19.2 g (57.2 mmol)was mixed with 100 mL of methanol and to this was added with stirring 7.7 mL (86 mmol) of methyl acrylate and 3.3 mL of 25 percent sodium methoxide in methanol. After 2 hours at ambient temperature, the mixture was heated to reflux for about 2.5 hours during which time another 10 mL of 25 percent sodium methoxide in methanol was added. The mixture was stirred at ambient temperature overnight and then another 5 mL of the 25 percent sodium methoxide in methanol was added and the mixture heated to reflux again for 2 hours. The resulting mixture was acidified with acetic acid and was then concentrated by evaporation under reduced pressure to obtain a tan solid. This was dissolved in 600 mL of dichloromethane and the solution obtained was washed 3×100 mL with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The tan, solid residue was flash chromatographed on silica gel (240-400 mesh, 5×20 cm (centimeter) column) eluting with mixtures of hexane and ethyl acetate ranging from 90:10 to 50:50. The second compound to elute was collected to obtain 12.6 g of the title compound as a nearly white solid melting at 160°-162° C. The proton NMR spectra of this was consistent with the assigned structure.

Workup

  1. additionto this was added
  2. temperaturethe mixture was heated
  3. additionwas added
  4. temperaturethe mixture heated
  5. temperatureto reflux again for 2 hours
  6. concentrationwas then concentrated by evaporation under reduced pressure
  7. customto obtain a tan solid
  8. customthe solution obtained
  9. washwas washed 3×100 mL with water
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated by evaporation under reduced pressure
  12. customchromatographed on silica gel (240-400 mesh, 5×20 cm (centimeter) column)
  13. washeluting with mixtures of hexane and ethyl acetate ranging from 90:10 to 50:50
  14. washThe second compound to elute
  15. customwas collected

Sources & evidence

ORD record
ord-522ebffcf32c478999cd8b37620c9189
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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