products that were insoluble in all common solvents and no molecular weights have been deteriiiincd. The yields of I, I1 and I11 are 40, 20 and 4OCi;, respectively, based on the thiophene reacted, wheii two moles of thiophene was treated with one mole of formaldehyde and three moles of arnmnniuru chloride. The cxccss reactxnts were recovcr:ililc. .Ittcnipts to irnl)rove the yields of I ~ i i i ( 1IT ;ire being ni:tdc. 1~r:xaiiiethylenetetraiiiiiic was fouiid to react with thiophene i i i the presence of conceiitratetl hyrlrochloric acid to give 7% of I, 25% of I1 arid of I11 on a weight per cent. basis. perficially, a t least, this reaction appcar’s io br siiiiilnr to the hlannich rcxction with ketones. I t tliffers in that free amine bases ant1 forma1dt.hyde appear not to react and that primary and secondary amine hydrochlorides do n(Jt react as rapidly as ammonium chloride. h preliniinary study of the reaction with thiophene derivatives indicates wide applicability. Full details of the reaction with such derivatives as 2- and 3-methylthiophene, 2-chlorothiophene, and 2-t-butylthiophene will be reported in a later coininunication.
follows: 0.3 i d . of an acid hydrolysate (1.13 mg. protein), 20 mg. of PIPSYLchloride, and excess sodiuin carbonate were shaken in a Folin tube a t 90’ for ten minutes. The walls were washed down, 5 mg. of labelled reagent added and the procedure repeated. One 1111. of ammonia was added. The mixture, together with an acetone soliltinn of some snlid renction products, was xldctl to 200 iiig. of noriu:tl 1’II’SYI,glycii~e in ~ I ~ I I I ~ O I acidified, I~;~, cxtracted with wbutanol, and iodobeiizeiiesulfoiiate ion removed by passing the butanol over Duolite C3 (ion eschange resin). Ligroin was added and the carrier extracted into alkali and purified by repeated precipitation by acid, solution in ainmonia, arid treatment with activated charcoal, the amount a t any stage" bcing estimated sPectrc.,E)li(Jtoiiietricallya t 2500 A. and its radioactivity measured in solution with a Geiger couiiter. Values obtained a t stages of purification corresponding to carrier recoveries of about 12.5, 10 and 7.5 were 1.59, 1.52 and 1.54% glycine for one analysis and 1.52, 1.52 and 1.5076 for another. Rittenberg and Foster reported 1.57,.‘ Less than one-hundredth per cent. of d ( -)alanine was found in the P-lactoglobulin hydrolysate using PIPSE’L d( -)alanine carrier. Seven and four-tenths per cent. of alanine wits found when 1). 13ARTOUCH S o C O N Y - V A C U U M L A B O R A T O R I E S HOWARD 1 ) I v r s I o x VF SOCONY-VACUUM OIL Co., INC. racemic carrier was employed. Chibnall reported I
