Methyl iodide → 2-[5-(Methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamide

HRID 255819Notes

Reaction equation

HRID 255819 reaction equation
[OH-].[K+].[SH:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])=[N:6][N:5]=1.[CH3:20]I>CO>[CH3:20][S:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 14797Potassium HydroxideHCID 178514763HCID 178514763, compound

Product 1

HCID 139587772-[5-(Methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamideYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a solution containing 0.62 g of potassium hydroxide in 50 ml of methanol was added 3 g of the oxadiazole prepared in Example 2. After stirring about five minutes, 2 g of methyl iodide was added. The suspension was refluxed 0.5 hour, cooled to 30° C., an extra 10 g of methyl iodide was added, and the suspension was refluxed an additional two hours, then concentrated in vacuo. After water was added to the residue, the suspension was filtered and the solid was washed with 1×50 ml of water. The suction-dried solid was recrystallized from 2-propanol to give 2 g of the subject compound: m.p. 138°-140° C.

Workup

  1. temperatureThe suspension was refluxed 0.5 hour
  2. temperaturethe suspension was refluxed an additional two hours
  3. concentrationconcentrated in vacuo
  4. additionAfter water was added to the residue
  5. filtrationthe suspension was filtered
  6. washthe solid was washed with 1×50 ml of water
  7. customThe suction-dried solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-9e460c7480e8413aa94d306a53f0da2f
Source dataset
uspto-grants-1987_10
Patent number
US04699649

Reaction notes

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