Acetylenic Amines. III. The Haloethynyl Derivatives - Journal of

C. W. Ryan, Nelson R. Easton, Robert D. Dillard, and Francis G. Henderson. J. Med. Chem. , 1962, 5 (4), pp 780–784. DOI: 10.1021/jm01239a011. Public...
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C. W. RYAN, N. R. EASTON, R. D. DILLARD, AND F. G. HENDERSON Voi. 5

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taken t o dryness under vacuum on a steam bath. The residue was crystallized from ethanol to give 6.7 g. (62.5%) of 3-methyl-5-ethyl-6-phenyl-meta-thiazane2,4-dione, m.p. 99-100". Anal. Calcd. for ClsH1;,NOcS:C, 62.62;H. 6.07; S , 5.62. Found: C, 63.33; H, 6.33;K,5.28. Action of Hydrogen Peroxide on the Dione.--A mixture of 10.0 g. (0.043 mole) of the dione, 100 nil. of glarial acetic arid and 15 ml. of 30% hydrogen peroxide \vas stirred for 19 hr. :It room temperature. A11 of thc solvmts were then removed under vicuiim while heating on a stearn tmth. .4 glassy residue was obtained which when rc4luxed with cliloroforrn gave a white solid. The chloroform solution was cooled arid filt,ered to give