Tetrahydrofuran → N-(4-chloro-3-methyl-5-isoxazolyl)-2-(4-dimethylaminobenzyl)benzo[b]thiophene-3-sulfonamide

HRID 2270678Notes

Reaction equation

HRID 2270678 reaction equation
[Cl:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH2:7].[H-].[Na+].[CH3:11][N:12]([CH3:33])[C:13]1[CH:32]=[CH:31][C:16]([CH2:17][C:18]2[S:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19]=2[S:27](Cl)(=[O:29])=[O:28])=[CH:15][CH:14]=1.C1COCC1>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[NH:7][S:27]([C:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[S:22][C:18]=1[CH2:17][C:16]1[CH:15]=[CH:14][C:13]([N:12]([CH3:11])[CH3:33])=[CH:32][CH:31]=1)(=[O:28])=[O:29]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 105828224-Chloro-3-methyl-1,2-oxazol-5-amineHCID 229984572-(4-Dimethylaminobenzyl)-benzo[b]thiophene-3-sulfonylchloride

Product 1

HCID 10115600N-(4-chloro-3-methyl-5-isoxazolyl)-2-(4-dimethylaminobenzyl)benzo[b]thiophene-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

N-(4-chloro-3-methyl-5-isoxazolyl)-2-(4-dimethylaminobenzyl)-benzo[b]thiophene-3-sulfonamide was prepared by the method of Example 41 with 4-chloro-3-methyl-5-aminoisoxazole (0.52 mmoles, 69 mg), NaH (1.3 mmoles, 31 mg), 2-(4-dimethylaminobenzyl)-benzo[b]thiophene-3-sulfonylchloride (0.58 mmoles, 0.21 g) and THF (4 ml). Flash chromatography (5% methanol/chloroform) provided 0.16 g (66%) of a yellow gummy solid, m.p. 105-1 10° C.

Sources & evidence

ORD record
ord-bd04ce0d6d3747bc8ce4b0cadda9d6b0
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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