Sodium hydride → N-(4-bromo-3-methyl-5-isoxazolyl)-2,5-dimethyl-furan-3-sulfonamide

HRID 234407Notes

Reaction equation

HRID 234407 reaction equation
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH2:7].[H-].[Na+].[CH3:11][C:12]1[O:13][C:14]([CH3:21])=[CH:15][C:16]=1[S:17](Cl)(=[O:19])=[O:18]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH:7][S:17]([C:16]1[CH:15]=[C:14]([CH3:21])[O:13][C:12]=1[CH3:11])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27950242,5-dimethylfuran-3-sulfonyl ChlorideHCID 104875194-Bromo-3-methylisoxazol-5-amine

Product 1

HCID 23445350N-(4-bromo-3-methyl-5-isoxazolyl)-2,5-dimethyl-furan-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-2,5-dimethyl-furan-3-sulfonamide was prepared by the method of Example 41 with 4-bromo-3-methyl5-amino-isoxazole (2.0 mmoles, 0.35 g), NaH (5.0 mmoles, 200 mg), 2,5-dimethyl-furan-3-sulfonylchloride (2.4 mmoles, 0.47 g) and THF (9 ml). Flash chromatography (5% methanol/chloroform) followed by recrystallization from chloroform and hexanes provided 0.21 g (31%) of a light brown solid, m.p. 85.5°-87° C.

Workup

  1. customFlash chromatography (5% methanol/chloroform) followed by recrystallization from chloroform and hexanes

Sources & evidence

ORD record
ord-8292ffc72e4b4db3849458f77e3aa1d0
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

Loading…