Hydrochloric Acid → HCID 18509230, compound

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[C:4]([C:20]([O:22]C)=[O:21])[CH:3]=1.Cl>CO.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([C:20]([OH:22])=[O:21])[C:5]([N:6]([CH3:17])[S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[CH:18][CH:19]=1

Participants

Procedure

To a suspension of 4′-chloro-2′-methoxycarbonyl-N-methyl-p-toluenesulfonanilide (13.3 g (37.5 mmol)) in methanol (30.0 ml), 10% aqueous sodium hydroxide solution (30.0 ml) was added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 48 hours, and then concentrated under reduced pressure. Water was added to the residue to get a homogeneous solution, followed by addition of concentrated hydrochloric acid (10.0 ml) to bring about precipitation of crystals. To this, ethyl acetate was added to extract the product. The extract was then washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diethyl ether was added to the crystals. The crystals were collected by filtration and washed to give 10.4 g (82%) of the title compound as white crystals.