5-Amino-3,4-dimethylisoxazole → N-(3,4-dimethyl-5-isoxazolyl)-2-(carbomethoxy)thiophene-3-sulfonamide

HRID 2270586Notes

Reaction equation

HRID 2270586 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](Cl)(=[O:12])=[O:11])=[O:4].[NH2:14][C:15]1[O:19][N:18]=[C:17]([CH3:20])[C:16]=1[CH3:21]>N1C=CC=CC=1>[CH3:20][C:17]1[C:16]([CH3:21])=[C:15]([NH:14][S:10]([C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])(=[O:12])=[O:11])[O:19][N:18]=1

Participants

4

Reactant 2

HCID 883175-Amino-3,4-dimethylisoxazoleHCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

Product 1

HCID 10615322N-(3,4-dimethyl-5-isoxazolyl)-2-(carbomethoxy)thiophene-3-sulfonamideYield 79.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methoxycarbonylthiophene-3-sulfonyl chloride (2.50 g, 10.05 mmol) was added to a solution of 5-amino-3,4-dimethylisoxazole(0.98 g, 8.75 mmol) in dry pyridine (5.0 ml). The reaction mixture was stirred at room temperature for 16 h. Pyridine was removed under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was washed with 1 N HCl (2×50 ml) and dried over anhydrous magnesium sulfate. Evaporation of the solvents left an oily residue, which, after purification by column chromatography over silica gel (1:1 hexanes/ethyl acetate as eluent), yielded 2.20 g (65%) of a brown solid. Further purification was achieved by recrystallization from ethyl acetate/hexanes, giving the pure product as a white solid, m.p. 113-116° C.

Workup

  1. customPyridine was removed under reduced pressure
  2. customthe residue was partitioned between water and dichloromethane
  3. washThe organic layer was washed with 1 N HCl (2×50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvents
  6. waitleft an oily residue, which
  7. customafter purification by column chromatography over silica gel (1:1 hexanes/ethyl acetate as eluent)

Sources & evidence

ORD record
ord-967c6bc4fb904b1fa53a6dd7913455c9
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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