Methyl iodide → 2-[[5-(Methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

HRID 231975Notes

Reaction equation

HRID 231975 reaction equation
[OH-].[K+].[SH:3][C:4]1[S:8][C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH2:19])(=[O:18])=[O:17])=[N:6][N:5]=1.[CH3:20]I>CO>[CH3:20][S:3][C:4]1[S:8][C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH2:19])(=[O:18])=[O:17])=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 14797Potassium HydroxideHCID 1785147042-[(5-Mercapto-1,3,4-thiadiazol-2-yl)methyl]benzenesulfonamide

Product 1

HCID 159257222-[[5-(Methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamideYield 15.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution containing 1.0 g of potassium hydroxide in 50 ml of methanol was added 5 g of the crude oxadiazole prepared in Example 2. After stirring about five minutes, 3.5 g of methyl iodide was added. The solution was refluxed one hour, cooled to 30°, an extra 10 ml of methyl iodide was added, and the solution was refluxed an additional two hours, then concentrated in vacuo. After water (about 150 ml) was added to the residue, the suspension was extracted with methylene chloride. The methylene chloride solution was dried (MgSO4), concentrated in vacuo, and the residue was recrystallized from acetonitrile to give 0.8 g of the subject compound; m.p. 175°-178° C. NMR(CDCl3, DMSO-d6): δ 2.8(s, SCH3); 4.9(s, CH2); 7.3(s, NH2); 7.4-8.3 (m, ar) ppm. Mass spectrum by direct probe using electron impact ionization showed highest significant m/e 301.

Workup

  1. temperatureThe solution was refluxed one hour
  2. temperaturecooled to 30°
  3. temperaturethe solution was refluxed an additional two hours
  4. concentrationconcentrated in vacuo
  5. additionAfter water (about 150 ml) was added to the residue
  6. extractionthe suspension was extracted with methylene chloride
  7. dry with materialThe methylene chloride solution was dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-70088dd011c54e64ab8060a52db7d83c
Source dataset
uspto-grants-1989_07
Patent number
US04851030

Reaction notes

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