Reaction of ethyl 9-thioacridonyl-10-acetate with hydrazine

✍ Scribed by A. A. Martynovskii; I. V. Mel'nik; N. A. Klyuev; V. L. Rusinov; A. I. Panasenko

• Book ID: 104783272
• Publisher: Springer US
• Year: 1989
• Tongue: English
• Weight: 341 KB
• Volume: 25
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00480761

✦ Synopsis

flux condenser and immersed in a thermostat at the required temperature, was placed 12.5 mmole halide I or II, 105 mmole alkyl chloride, 15 ml chloroform, and the required quantity of catalyst and potassium carbonate, and the mixture was stirred for 3 or 5 h. The solid deposit was filtered off and washed with chloroform.

The filtrate was evaporated in vacuum and the individual compounds isolated by chromatographing the residue on a column of silica gel with 6:6:1 chloroform-acetonitrile-water.

The ratio of the reaction products was determined by liquid chromatography after removing resinous substances from the reaction mixture on a short column of silica gel. Salt VIII, C22H2~NBr , mp 144-145~ XI, C29H~0NBr, mp 236-237~ B.

To a mixture of 2.53 g (12.5 mmole) halide I, 12.1 ml (105 mmole) benzyl chloride, and 0.142 g (0.625 mmole) TEBA-CI in a current of nitrogen was added 18 ml 25% NaOH. This was stirred (~i000 rpm) for 3 h in a thermostat at 45~

The aqueous layer was extracted with chloroform,:the extract combined with the organic layer and evaporated in vacuum. The residue was recrystallized from water. Yield 1.7 g compound XII, C29H30NC1, mp 205-206~ LITERATURE CITED