2-Thiophenesulfonyl chloride → N-(4-Bromo-5-methyl-3-isoxazolyl)thiophene-2-sulfonamide

HRID 234305

Reaction equation

HRID 234305 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[NH2:10][C:11]1[C:15]([Br:16])=[C:14]([CH3:17])[O:13][N:12]=1>N1C=CC=CC=1>[Br:16][C:15]1[C:11]([NH:10][S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:7])=[N:12][O:13][C:14]=1[CH3:17]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 27744644-Bromo-5-methyl-1,2-oxazol-3-amine

Product 1

HCID 22998411N-(4-Bromo-5-methyl-3-isoxazolyl)thiophene-2-sulfonamideYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Thiophene-2-sulfonyl chloride (183 mg, 1 mmol) was added to a solution of 3-amino-4-bromo-5-methylisoxazole (177 mg, 1 mmol) in dry pyridine (0.5 ml). The reaction mixture was stirred at room temperature for 3 h. Pyridine was removed under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was washed with 1N HCl (3×10 ml), brine (10 ml) and dried over anhydrous magnesium sulfate. Evaporation of the solvents left an oily residue which was solidified at -20° C. and then purified by recrystallization from ethyl acetate/hexanes, to give the pure product (51% yield) as a tan solid, m.p. 156°-158° C.

Workup

  1. customPyridine was removed under reduced pressure
  2. customthe residue was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with 1N HCl (3×10 ml), brine (10 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvents
  6. waitleft an oily residue which
  7. customwas solidified at -20° C.
  8. custompurified by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-98c55c648c034017af90ed529e7f7646
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Linked notes

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