Ammonia → 2-(4,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)benzenesulfonamide

HRID 255825Notes

Reaction equation

HRID 255825 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[O:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14](Cl)(=[O:16])=[O:15])=[N:3]1.[NH3:18]>O1CCCC1>[CH3:1][N:2]1[C:6](=[O:7])[O:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[S:14]([NH2:18])(=[O:16])=[O:15])=[N:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 139588562-(4,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)benzenesulfonyl chloride

Product 1

HCID 139588572-(4,5-Dihydro-4-methyl-5-oxo-1,3,4-oxadiazol-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 3.3 g of the product of Example 3 in 50 ml of tetrahydrofuran was added dropwise 3 ml of condensed ammonia while keeping the reaction temperature at -5° C. with external cooling. After stirring at 0° C. for 1.5 hours, the solvent was evaporated in vacuo and water was added to the residue to yield a precipitate. After filtration the isolated residue was washed with water, then dissolved in tetrahydrofuran and dried over MgSO4. After evaporation of the solvent in vacuo, 2.9 g of the subject compound was obtained as a crude solid; m.p. 168°-173° C.

Workup

  1. additionwas added dropwise
  2. customat -5° C.
  3. customthe solvent was evaporated in vacuo and water
  4. additionwas added to the residue
  5. customto yield a precipitate
  6. filtrationAfter filtration the isolated residue
  7. washwas washed with water
  8. dissolutiondissolved in tetrahydrofuran
  9. dry with materialdried over MgSO4
  10. customAfter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-25b1c7e0023f4ae982d04c1a3ead7cf1
Source dataset
uspto-grants-1987_10
Patent number
US04699647

Reaction notes

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