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Bis(2-chloroalkyl) amides of N-acetylphenylalanine.     Nemets, V. G.; Blinova, G. G.; Zhilinskaya, T. D.    Lensovet Leningr. Tekhnol. Inst.,  Leningrad,  USSR.    Zhurnal Obshchei Khimii  (1967),  37(4),  817-19.  CODEN: ZOKHA4  ISSN: 0044-460X.  Journal  written in Russian.    CAN 67:116692    AN 1967:516692    CAPLUS
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Abstract
To 3.1 g. PhCH2CH(NHAc)CO2H in AcCl was added slowly 4.2 g. PCl5 at -15 and the mixt. kept 3 hrs., evapd. <0 and filtered to give 64.7% PhCH2CH(NHAc)COCl, m. 103-4, which with (MeCHClCH2)2NH in C6H6 in the presence of Et3N overnight gave after sepn. of the pptd. amine salt and evapn. of the filtrate 91.9% PhCH2CH(NHAc)CON(CH2CHMeCl)2 (I), which darkened on standing; the glassy product slowly developed a content of ionic Cl.  Potentiometric titrn. with alkali consumed after 1 month storage, 0.085 equiv. base/2 moles of the substance.  Ir spectrum is reported.  Evidently I also undergoes the amide-ester rearrangement to which the analogous 2-chloroethyl compd. is very susceptible in storage (Ross and Wilson, CA 54: 8584h).
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