Sodium hydride → HCID 10274461, compound

HRID 234402Notes

Reaction equation

HRID 234402 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH2:8])[O:4][N:3]=1.[H-].[Na+].[Cl:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16][C:17]2[S:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[C:18]=2[S:26](Cl)(=[O:28])=[O:27])=[CH:14][CH:13]=1>C1COCC1>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:26]([C:18]2[C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[S:21][C:17]=2[CH2:16][C:15]2[CH:14]=[CH:13][C:12]([Cl:11])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 883175-Amino-3,4-dimethylisoxazoleHCID 22998492HCID 22998492, compound

Product 1

HCID 10274461HCID 10274461, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(3,4-dimethyl-5-isoxazolyl)-2-(4-chlorobenzyl)-benzo[b]thiophene-3-sulfonamide was prepared by the method of Example 41 with 3,4-dimethyl-5-aminoisoxazole (1.2 mmoles, 1.4 g), NaH (3.0 mmoles, 73 mg), 2-(4-chlorobenzyl)-benzo[b]thiophene-3-sulfonylchloride (1.4 mmoles, 0.50 g) and THF (8 ml). Flash chromatography (50% ethyl acetate/hexanes) followed by recrystallization from methanol and water provided 1.04 g (27%) of a yellow solid, m.p. 100°-102° C.

Workup

  1. customFlash chromatography (50% ethyl acetate/hexanes) followed by recrystallization from methanol and water

Sources & evidence

ORD record
ord-68928051b892488eb93e1be69ba0d19e
Source dataset
uspto-grants-1997_01
Patent number
US05594021

Reaction notes

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