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

HRID 1898963Notes

Reaction equation

HRID 1898963 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-0859ad19deed425bb7ba3988b5054935
Source dataset
uspto-grants-1996_11
Patent number
US05571826

Reaction notes

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