Acridone → HCID 66701480, compound

Participants

Reaction Conditions

Reaction Steps

15 g of 9(10H)acridone (manufactured by Wako Pure Chemical Industries, Ltd.) and 3.4 g of sodium hydroxide (manufactured by Wako Pure Chemical Industries, Ltd.) were dissolved in 84 g of dimethyl sulfoxide (manufactured by Wako Pure Chemical Industries, Ltd.), and the solution was heated to 45° C. 17.6 parts of CMS-P (manufactured by Seimi Chemical Co., Ltd.; chloromethylstyrene) was added dropwise to the solution, and the mixture was subjected to heating and stirring for further 5 hours at 50° C. This reaction liquid was poured under stirring into a mixed solution of 30 g of distilled water and 30 g of methanol (manufactured by Wako Pure Chemical Industries, Ltd.), and the resulting precipitate was separated by filtration and washed with 300 g of a solution prepared by mixing equal amounts by weight of distilled water and methanol. The resulting solids were dried under reduced pressure, and thus 17.5 g of 10-[(styrenyl)methyl]-9-acridanone was obtained as pale yellow solids. 175 g of N-methylpyrrolidone (manufactured by Wako Pure Chemical Industries, Ltd.) was added to 17.5 g of 10-[(styrenyl)methyl]-9-acridanone and 60.9 g of thioglycerol (manufactured by Sigma-Aldrich Co.), and the mixture was heated to 65° C. and stirred for 30 minutes under a nitrogen atmosphere. Subsequently, 0.14 g of V-65 (trade name, manufactured by Wako Pure Chemical Industries, Ltd.; 2,2′-azobis(2,4-dimethylvaleronitrile) was added thereto, and the mixture was stirred for 2 hours. 500 g of a mixed solvent of water/methanol (mixture at a weight ratio of 1:1) was added to the reaction solution, and the crystals crystallized out therefrom were separated by filtration and were washed using 100 g of methanol. The obtained solids were dried under reduced pressure, and 22.0 g of M-1 was obtained as pale yellow solids.

Provenance & Evidence