Derivatives of Aromatic Sulfinic Acids. II. The Reaction of Thionyl

Harry F. Herbrandson, Richard T. Dickerson Jr., and Julius Weinstein. J. Am. Chem. Soc. , 1956, 78 (11), pp 2576–2578. DOI: 10.1021/ja01592a068. Pub...
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H. F. HERBRANDSON, R. T. DICKERSON, JR.,

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amine were removed under reduced pressure and the resulting viscous red oil was distilled. The fraction that boiled a t 135-148' (1 b ) , n 2 51.5204, ~ weighed 21 g. (85y0). Anal. Calcd. for CljH24N20: NAP,5.62. Found: NAP, 5 .GI N- (2-Cyanoethyl) -N(4-isopropylbenzyl) -dichloroacetamide.-The following is an example of the general procedure employed for the preparation of the haloacetamides (see Tables I11 and IV). A mixture of 20.2 g. (0.1 mole) of N-(2-cyanoethyl)-4-isopropylbenzylamine, 125 ml. of a 1 N sodium hydroxide