Sodium Hydroxide → HCID 13519112, compound

HRID 1607531Notes

Reaction equation

HRID 1607531 reaction equation
[OH-].[Na+].[CH3:3][C:4]([S:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)([CH3:10])[C:5]([O:7]CC)=[O:6]>O.CO>[CH3:10][C:4]([S:11][C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)([CH3:3])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14599937Ethyl 2-methyl-2-(4-pyridinylthio)propanoate

Product 1

HCID 13519112HCID 13519112, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.7 grams NaOH in 5 ml of water was added dropwise to a solution of 8.79 grams of ethyl 2-methyl-2-(4-pyridinylthio)propionate in 15 ml methanol. The solution was stirred at room temperature overnight, and then concentrated in vacuo to remove methanol. Concentrated HCl was added to the sodium salt and the mixture triturated with isopropanol and heated on the steam bath. The mixture was then cooled and filtered to remove sodium chloride. The filtrate was concentrated in vacuo and the resulting gummy solid dissolved by adding hot isopropanol. The mixture was cooled and filtered to give the title compound. The filtrate upon concentration and cooling gave a further yield of the title compound. M.P. 190°-192° C.; 1NMR and IR were both in agreement for the titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove methanol
  3. additionConcentrated HCl was added to the sodium salt
  4. customthe mixture triturated with isopropanol
  5. temperatureheated on the steam bath
  6. temperatureThe mixture was then cooled
  7. filtrationfiltered
  8. customto remove sodium chloride
  9. concentrationThe filtrate was concentrated in vacuo
  10. dissolutionthe resulting gummy solid dissolved
  11. additionby adding hot isopropanol
  12. temperatureThe mixture was cooled
  13. filtrationfiltered

Sources & evidence

ORD record
ord-ec7aef09ccb64264b6d5a7e0bfba6da4
Source dataset
uspto-grants-1989_09
Patent number
US04866068

Reaction notes

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