4-(Chlorosulfonyl)benzoic acid → HCID 10641632, Verbindung
Reaktionsgleichung
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:23]=1[NH:22][CH:21]=[C:20]2[Cl:24]>N1C=CC=CC=1>[Cl:24][C:20]1[C:19]2[C:23](=[C:15]([NH:14][S:2]([C:5]3[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=3)(=[O:4])=[O:3])[CH:16]=[CH:17][CH:18]=2)[NH:22][CH:21]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
2.82 g (12.8 mmol) of 4-(chlorosulfonyl)benzoic acid and 1.42 g (8.54 mmol) of 7-amino-3-chloro-1H-indole were reacted with each other in pyridine at room temperature under stirring overnight, to give 2.33 g of 4-[N-(3-chloro-1H-indole-7-yl)sulfamoyl]benzoic acid. To 303 mg (0.86 mmol) of the product were successively added 260 μl of dimethylformamide, 204 μl (0.95 mmol) of diphenylphosphorylazide, 132 μl (0.95 mmol) of triethylamine and 113 μl (0.94 mmol) of 2-(2-aminoethyl)pyridine, followed by stirring at room temperature overnight. After concentrating, ethyl acetate and an aqueous saturated sodium bicarbonate were added thereto. The organic layer was separated and washed with brine. After evaporating the solvent, the residue was purified by silica gel column chromatography, to give 175 mg of the title compound.