GB818517A - Aziridino-quinones and hydroquinones - Google Patents

Abstract

The invention comprises 2 : 6-bis-aziridino-1 : 4 - benzhydroquinone, 2 : 6 - bis - aziridinobenzoquinone and 2 : 3 : 6-tris-aziridino-1 : 4-benzoquinone. 2 : 6-Bis-aziridino-1 : 4-benzhydroquinone and 2 : 3 : 6 - tris - aziridino - 1 : 4-benzoquinone are made by reacting a 2 : 6-dialkoxy-1 : 4-benzoquinone, in which the alkyl groups preferably have 1-4 carbon atoms, with an excess of aziridine, at or below room temperature and preferably below 0 DEG C., under anaerobic conditions, e.g. in an atmosphere of nitrogen, in an inert diluent such as an alkanol of 1-4 carbon atoms, e.g. methanol, and subsequently separating the two reaction products, for example by leaching out the soluble 2 : 3 : 6-tris-aziridino-benzoquinone with cold acetone, benzene or chloroform to leave a residue of 2 : 6 - bis - aziridino - 1 : 4 - benzhydroquinone. 2 : 6 - Bis - aziridino - benzoquinone is made by oxidizing 2 : 6-bis-aziridino-1 : 4-benzhydroquinone, suitably by treatment with p-benzoquinone in an aqueous, organic or aqueous organic reaction medium. In examples: (1) 2 : 6 - dimethoxy - 1 : 4 - benzoquinone is treated with aziridine in methanol, the precipitated product is extracted with benzene to leave a residue of 2 : 6-bis-aziridino-2 - 4-benzhydroquinone (recrystallized from dioxane) and a solution of 2 : 3 : 5-tris-aziridino-1 : 4-benzoquinone (recrystallized from ethyl acetate) and (2) the bis-aziridino compound from (1) is oxidized with p-benzoquinone to give 2 : 6-bis-aziridino-1 : 4-benzoquinone.