Studies of Phenothiazine. III. The Conversion of Phenothiazine to

Phenothiazine Derivatives: Di-oxygenated Compounds. David F. Houston , E. B. Kester , Floyd. DeEds. Journal of the American Chemical Society 1949 71 (...
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IroUb h 3 S E S R C H L)IVISIUN C O N T R I E ~ I O NNU. 369 PRUhf T f k HUREAU OF &ESffSTRY ANU kkliLS, UNITRD STATES DEPARTMENT OF AGRICULTURE, A T THE DEPARTMENT OF PflARNACOLOCY, STANFORD UNIVERSITY SCHOOL OF MEDICINE 1

Studies of Phenothiazine. 111. The Coitversiari eif Ptierikjthiazine to Thionai I ~ YFt.drt) DEEDSA N D C. W. EDDY

The growing iiiterest in the subject of biological phcnthiazonc) dcslgiiatcd as oxithiodipheiiylaoxidations and reductions together with the de- iniiie. Siniiiiikly, lijdiciiy$iiiiitfiiizh~i iiid its sirability of increasing the number of oxidatioii - leut% base, leuco liydrox"phenthiaionc, weii: reduction indicators is sufficient justification for kriowii as dioxythiodipheiiy imide aiid dioxythiothe description of a simple method for the conver- dipheriylarninc, respe;.'fively. sion of phenothiazine to hydroxyphenthiazone, I3ernthsen2 described a rncthod !or ihi? prcparaiiori of t hibriiil fiorii phehothiaiirk, hhikh &&hds tipod bxiddtioti inore commonly known as thionol. Phenthiazone and hydroxyphcnthiazoiie (see in a gtrotigly atld mcdluni. Fob each 50 g. at pHhothlaformulas I and 11) are the simplest thiazines t l i i b 1 kg. of concentkLte& slllf&k rtcld diluted 6 t h 2dO cc. of water is pddcd to the phenot,hiazine and the tnixture which in the presence of their respective leuco hFatcd a t 150 to 160"fortwenty-five hours. The isolation bases show the properties of reversible oxidation-- of the resulting thionol is raiher laborious and the yieid reduction systems.

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