Sodium hydride → N-(4-chloro-3-methyl-5-isoxazolyl)-2-ethylbenzo[b]furan-3-sulfonamide

HRID 1251762Notes

Reaction equation

HRID 1251762 reaction equation
[Cl:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH2:7].[H-].[Na+].[CH2:11]([C:13]1[O:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[C:14]=1[S:22](Cl)(=[O:24])=[O:23])[CH3:12]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH:7][S:22]([C:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[O:17][C:13]=1[CH2:11][CH3:12])(=[O:23])=[O:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 105828224-Chloro-3-methyl-1,2-oxazol-5-amineHCID 229984082-Ethylbenzo[b]furan-3-sulfonyl chloride

Product 1

HCID 10132084N-(4-chloro-3-methyl-5-isoxazolyl)-2-ethylbenzo[b]furan-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-chloro-3-methyl-5-isoxazolyl)-2-ethylbenzo[b]furan-3-sulfonamide compound was prepared by the method of Example 41 with 4-chloro-3-methyl-5-amino-isoxazole (1.0 mmols, 0.13 g), NaH (2.5 mmols, 60 mg), 2-ethylbenzo[b]furan-3-sulfonyl chloride (1.2 mmols, 0.28 g) and THF (7 ml). Flash chromatography (20% ethyl acetate/hexanes) followed by recrystallization from chloroform and hexane provided 97 mg (28%) of a white solid, m.p. 132-133.5° C.

Workup

  1. customFlash chromatography (20% ethyl acetate/hexanes) followed by recrystallization from chloroform and hexane

Sources & evidence

ORD record
ord-5cd8395d00bd4dfe8f8b4de7257f1ec8
Source dataset
uspto-grants-2002_01
Patent number
US06342610B2

Reaction notes

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