Benzenesulfonyl chloride → Desaminosulfamethoxazole

HRID 1899685Notes

Reaction equation

HRID 1899685 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH3:7][C:5]1[O:4][N:3]=[C:2]([NH:1][S:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:16])=[O:15])[CH:6]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 661723-Amino-5-methylisoxazole

Product 1

HCID 747064DesaminosulfamethoxazoleYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Amino-5-methylisoxazole (0.196 g, 2.0 mmol) was dissolved in dry pyridine (3 ml). Benzenesulfonyl chloride (0.352 g, 2.0 mmol) was added and the resultant solution stirred at room temperature for 16 h. Pyridine was removed under reduced pressure. The residue was dissolved in dichloromethane (75 ml) and washed with 1N HCl (2×50 ml). The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give N-(5-methy-3-isoxazolyl)benzene-sulfonamide (0.40 g, 84% yield). The product was purified by recrystallization using ethyl acetate/hexanes to give a white solid, m.p. 107°-8° C.

Workup

  1. customPyridine was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (75 ml)
  3. washwashed with 1N HCl (2×50 ml)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1bc7604072024a988114ace4596f27d7
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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