Ammonia → 3,5-Dimethylisoxazole-4-sulfonamide

HRID 1914718Notes

Reaction equation

HRID 1914718 reaction equation
[CH3:1][C:2]1[C:6]([S:7](Cl)(=[O:9])=[O:8])=[C:5]([CH3:11])[O:4][N:3]=1.[NH3:12].CO>C1COCC1>[CH3:1][C:2]1[C:6]([S:7]([NH2:12])(=[O:9])=[O:8])=[C:5]([CH3:11])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 27363193,5-Dimethylisoxazole-4-sulfonyl chloride

Product 1

HCID 49623033,5-Dimethylisoxazole-4-sulfonamideYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethylisoxazole-4-sulfonyl chloride (4.3 g; 21.8 mmol; 1 eq) is dissolved in THF (10 mL), ammonia in MeOH (55 mL; 2 M; 109 mmol; 5 eq) is added and the reaction is stirred for 1 h at room temperature. The reaction mixture is concentrated under reduced pressure and the residue is taken up in 100 mL of EtOAc. The organic phase is washed with a saturated aqueous solution of NH4Cl (100 mL) then dried over MgSO4. The solvent is removed under reduced pressure, affording 2.6 g (67%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.59 (s, 2H), 2.56 (s, 3H), 2.34 (s, 3H). HPLC (max plot) 96.5%; Rt 1.22 min.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. washThe organic phase is washed with a saturated aqueous solution of NH4Cl (100 mL)
  3. dry with materialthen dried over MgSO4
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-845e201062584f74b59af2b3a74510ac
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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