Acetic Acid → alpha-[2-(4-Aminosulfonylphenyl)ethylamino]-3-indoleacetic acid Hydrate

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To a stirred solution of 6.01 g (0.03 mmole) of 4-(2-aminoethyl)benzenesulfonamide and 2.5 mL (2.62 g 0.044 mole) of acetic acid in 150 mL of MeOH was added a solution of 2.64 g (0.03 mole) of methyl glyoxylate in 50 mL of MeOH followed by 2.93 g (0.025 mole) of indole. Initially a solution was obtained. Soon solid began separating. The resulting mixture was allowed to stand for four days. The solid was collected by filtration, washed with ether and dried give 3.72 g (38%) of the title compound as a buff solid, m.p. 226° C. (dec). The solid insoluble in CH2Cl2, MeOH, DMSO, DMF and acetic acid.

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