Acetic Acid → HCID 18985867, compound

HRID 2396682Notes

Reaction equation

HRID 2396682 reaction equation
[CH2:1]([S:8][C:9]1[N:13]2[C:14](SC)=[N:15][C:16]3[N:21]=[CH: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:24](OCC)(=[O:27])C=C.C[O-].[Na+].C(O)(=O)C>CO>[CH2:1]([S:8][C:9]1[N:13]=[C:12]2[N:11]([C:14]([O:27][CH3:24])=[N:15][C:16]3[N:21]=[CH: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

6

Reactant 4

HCID 176Acetic AcidHCID 8821Ethyl AcrylateHCID 10942334Sodium MethoxideHCID 18985861HCID 18985861, compound

Product 1

HCID 18985867HCID 18985867, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 17.7 g (52 mmol) of 3-benzylthio-5-methylthiopyrido[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine in 200 mL of methanol was prepared and to this was added at ambient temperature with stirring 8.5 mL (7.8 g, 78 mmol) of ethyl acrylate and 2.4 mL of 25 percent sodium methoxide in methanol (10 mmol). Everything dissolved fairly quickly and after 15 min new precipitate formed. After about 1 hour the mixture was acidified with acetic acid and the volatile components were removed by evaporation under reduced pressure. The residue was dissolved in dichloromethane and the resulting solution was washed with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was diluted with ether, recovered by filtration, and dried to obtain 14.6 g of the title compound as a brown powder melting at 282°-284° C. with decomposition.

Workup

  1. customwas prepared
  2. additionto this was added at ambient temperature
  3. dissolutionEverything dissolved fairly quickly and after 15 min new precipitate
  4. customformed
  5. customthe volatile components were removed by evaporation under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washthe resulting solution was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. additionThe residue was diluted with ether
  11. filtrationrecovered by filtration
  12. customdried

Sources & evidence

ORD record
ord-08fac89659dc4515a2a8dfbe314f4a17
Source dataset
uspto-grants-1996_02
Patent number
US05494887

Reaction notes

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