Hydrochloric Acid → N-(3,4-Dimethyl-5-isoxazolyl)-2-[1-(phenylsulfonyl)-1H-indol-2-yl]benzenesulfonamide

HRID 1585674Notes

Reaction equation

[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([N:8](COCCOC)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[N:19]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:11])=[O:10])[O:4][N:3]=1.Cl>CCO>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[N:19]([S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:28])=[O:29])[C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:10])=[O:11])[O:4][N:3]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of the title product of Step (C) (210 mg; 0.35 mmol), 6N HCl (5 ml) and EtOH (5 ml) was refluxed for 1.5 hours. A solid began precipitating during the reaction. After slowly cooling to 5° C., the suspension was filtered and the solid was washed with water. Drying afforded 154 mg (87%) of the title product of this Example as a cream colored solid. mp 207-209° C. (dec.; darkened at 196° C.); Rf=0.50, EtOAc (UV detection).

Workup

temperaturewas refluxed for 1.5 hours
customA solid began precipitating during the reaction
filtrationthe suspension was filtered
washthe solid was washed with water
customDrying

Sources & evidence

ORD record: ord-b44cc918e87b42d6b4b6c7382f2a0d70
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05939446

Reaction notes

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