Water → 1,2,5,6-Tetrahydro-1-methyl-3-(3-(2-ethylsulfinyl-1-ethoxy)-1,2,5-thiadiazol-4-yl)pyridine oxalate

HRID 2257929Notes

Reaction equation

HRID 2257929 reaction equation
[CH2:1]([S:3][CH2:4][CH2:5][OH:6])[CH3:2].C(SCC[O:12][C:13]1[C:14]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:15][S:16][N:17]=1)C.[CH3:24]S(O)(=O)=O.[OH-:29].[Na+].[OH2:31]>>[C:5]([OH:6])(=[O:12])[C:4]([OH:31])=[O:29].[CH3:24][N:20]1[CH2:21][CH2:22][CH:23]=[C:18]([C:14]2[C:13]([O:29][CH2:2][CH2:1][S:3]([CH2:4][CH3:5])=[O:31])=[N:17][S:16][N:15]=2)[CH2:19]1

Participants

6

Reactant 5

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 80752-(Ethylthio)ethanolHCID 14798Sodium HydroxideHCID 196125833-(4-(2-Ethylthio-1-ethoxy)-1,2,5-thiadiazol-3-yl)pyridine

Product 1

HCID 196125971,2,5,6-Tetrahydro-1-methyl-3-(3-(2-ethylsulfinyl-1-ethoxy)-1,2,5-thiadiazol-4-yl)pyridine oxalate

Procedure

1,2,5,6-tetrahydro-1-methyl-3-(3-(2-ethylsulfinyl-1-ethoxy)-1,2,5-thiadiazol-4-yl)pyridine oxalate was prepared in the same manner using 2-(ethylthio)ethanol as the starting alcohol. The intermediate 3-(4-(2-ethylthio-1-ethoxy)-1,2,5-thiadiazol-3-yl)pyridine was oxidized with 1.1 equivalent of NaIO4 and 1 equivalent MeSO3H using water as the reaction solvent. After a reaction time of 3.5 h. the solution was made basic with 2N NaOH and extracted with ethyl acetate. The combined extracts were dried over MgSO4 and evaporated under vacuum. The resulting sulfoxide was then converted to the title compound in the same manner described above. M.p. 171°-172° C., M+ : 302. Compound 45.

Workup

  1. customAfter a reaction time of 3.5 h.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried over MgSO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-7a5135b7b4994d5f8260823ed65379bb
Source dataset
uspto-grants-1997_08
Patent number
US05658932

Reaction notes

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