reported difficulties in obtaining a product with nip 118-120 '. I t is therefore of interest that, during chlorination, the resultiiig precipitate of I11 ronsisted initially of needles, followed hy tiny platelets; prior to extensive washing with I.;trO, the precipit tit(' melted in t x o steps under a microscope hot stage, mp 94 (p1att.lets) and LO:! (needles). These are obviously the t K O moniers Of I11 :tnd the nielting point of the final product will clearly depend on the ratio of the two anomer!: Ivhich, in turn, determine.< t i i r s ratio of the two anomeric nucleosides in llre roiiderisation rex('tion.19 Because of the lihility of 111, the freshly prepared mist urc of aiiomers was used :is such im1nedi:itely ill tlie subsequeni cwiidensation step. 1-( 3,5-Di-O-p-chlorobenzoyl-2-deoly-cu,P-D-ethyluracil (IF').--11 ( 1.49 g, 4.4 mriioles) was suspended in about I30 ml of anhydrous PhMe, vigorously stirred, and dried azeotropically by removal of about one-third of the solvent; :$.ti g of 111 (8.S Illmoles), previously dried, vas added rapidly, and the rnisture \vas heated 3 min, then cooled and filtered through glass wool. The precipitate was dissolved (CHCI,), ihe solution w i s washed (30(, KI, HZO), and the orgnic phase was dried (S:iZSO, 1. The s d t was filtered off, the CHCla solution was hrriuglit t o dryness, and the residue was dissolved in hot anhydrous CtOH. Crystallization occurred on cooling to give 1.1 g ( 4 7 ' , i ) of IT., melting at 154-178 and eshihiting urider a niicroscwpe hot s t a p
t,4',6,6'-Te trabromo-X,2'-biphenyldiol JIono(dihydrogen phosphate). .4 Neh Agent for Combating Distomatosis'
Attempted Separation of tlie Anomers of V by Ion-Exchange Br W \ B \ r Chromatography:---.I Dowex I - S 2 (200-400 mesh) (OH- I cdumn, 23 X 2 cni, WBS washed with 500 nil of 30( XleOH, and 15 nig of l' in the same solvent, deposi Br Br cwluniii. The latter was then xashed with 250 nil of GO' I aqueous hIeOIl mid 250 nil of !I0 aqueous 1IeOH. Tlie nucleositfe was then eluted with 0.05 SH4HCOI :it :t f l ~ r~~ ; ~ t e OND/OH of ahout I .5 ml/min and fractions uf 13 nil were collected. The nucleoside appeared in two fairly-nell-definetl pecks : fractioii 1 3 o'o l' (4.9 mg, mp 172-171.5") and fraction 16 (5.2 mg, nip 14:3-14iz\. I I Fraction 16, but not fraction 13, supported liacterial u i t l p l i a ~ e multiplicai.ion and is therefore the p :tnomer of \-. Separation of anomers of IV was avliieve deposited as 1.0-mrn layers on 20 X 15 c m I I solvent, system CHC1,-I;* 4.62 X I O 3 ) ; p K , = 9.9b. S m r spectra were determined in I)20 for earh of the momers a t 30" with a T'arian HA-100 spectrometer and .\lerSi its esterrial standard. Except for the added signals due tu tlie presence of :i 5-Et in place of a 5-LIe substituent, tlie spectra were similar t o those of the corresponding anomers of tli?mitii~ie:~~ for a-5-echyIIn (Hi, quartet!. = S.O cps, . / F ~ , ~ - , l ~ ~ ~ anoiner! 6.58 ppin (€11, triplet I = ~/11,,-1121
./ll,l..ll,l
Acknowledgments.- -\Ye are indebted to Professor X. Xriteunis (Service tle C:hiniie Orgnniquc, Viiiwrsitc tle Gent,, Belgium) for the iinir spectra. t o Professor C . Heitlell.)erger (1:iiiversit'y of \\-isconsin) for the tests of antirirul activity, uiid to Dr. I. Pietrzykowslrit aiitl Dr. A I . Piccliowska for tli n the gronth-supportiiig properties of the anom d tlic possihle niiitag,~iir
activity of @-5-ethyltleox> I. 1'. Josryh, E. I:. Schaub, nrid J. H. JYilliani?, J . Oru. rhem., 19. 1736 (1054). ( 2 0 ) 11. I'rystas arid 1:. garin, Co~~ectio71 Czech. (:/rem. ~ o ? t r n i u l i . ,31, 1U:
