June, 1937
DERIVATIVES OF U-HYDROXVPHENYLMERCLJRIC CHLORIDE
Mo., for a research grant €or the completion of this investigation.
Summary Equimolar condensations of monohydroxyphenols with saturated aliphatic aldehydes were studied. It was found that polymers result in quantitative yields. Upon slow pyrolysk, these
lIf5
polymers yield the corresponding saturated primary alkylphenols. These types of condensations are being extended t o unsaturated and aromatic aldehydes, reLucing saccharides as well as to ketones, particularly cyclic ketones (cyclopentanone, cyclohexanone, alkyl cyclohexanones and camphor). RECEIVED MARCH4, 1937
NEWYORK,N. Y.
[CONTRI3UTION FROM THE RESEARCH LABORATORIES O F THEUPJOHN COMPANY]
Some Derivatives of Ortho-Hydroxyphenylmercuric Chloride BY HANSP. ANDERSEN AND MERRILL C. HART In earlier reports it has been shown that variations in structure have a limited influence on bacteriostatic properties of organic mercury compounds, and that more complex structures were not as effective as mercury derivatives of hydrocarbons or phenols with limited substituents.2 One very effective mercurial was found to be ohydroxyphenylmercuric chloride, this compound also being bactericidal a t some dilutions.2 It seemed that possible derivatives of this compound could be prepared which would have similar properties. Some imide derivatives of phenylmercuric nitrate have been described as being used iii germicidal detergent or cosmetic cotnpositioiis.3 I n the present work some imide derivatives of ohydroxyphenylmercuric chloride have been prepared ai id their bacteriological properties evaluated.4 One has been found to be equally as good as the parent compound. I t w a s found that, in general, imide derivatives were readily formed in alkaline solution, especially if the imide contained a carbonyl group. An attempt was made to prepare derivatives of pyrrole, auramine, carbazole and piperidine but only in the case of piperidine was a product obtained in the form of the hydrochloride. This was formed in the absence of alkali. Although the simplest structures are most effective, it was thought that fatty acid derivatives might facilitate the in vivo activity by increasing diffusion inta the surfaces in contact with the (1) Hart and Andersen, THIS JOURNAL, 65, 2762 (1834). (2) Hart and Andersen, ibid., 6T, 1059 (1935). See also Photak and Leake, J . Pharmacol., 66, 265 (1936). (3) British Patent 432,689, July 31, 1935. (4) We are indebted to Mr. E A Gibson, Bacteriological Laboratory, for these results.
antiseptic. A few representative phenolmercuric fatty acid compounds have been prepared and described. The table gives the results obtained together with melting points and analytical data. TABLE r Compound with HOCsHiHgCl(o-) Succinimide Saccharine Phthalimide Piperidine Theobromine Barbituric acid Acetic acid Pelargonic dcirl Oleic acid Lauric acid Myristic acid Pdmitic arid Stearic acid
Yield,
% 72 3
53.7 96 3 79.3 51 48
...
60 7 ti4 a
74 72 !lo 70
hl. I,.,
'e.
232-235 242-243 223-224 126 145-165
...
150-151 13.5
!IS- 96 135.5-138.5 13S-l:lti' ix-i:ji 135-1378
1nhibitjng Mercury dilution t o analyses, % Slaph. a w e u s Calcd. Found in 5 min. 51.1 5 0 . 8 1--75,000"~" 42.5 43.1 1--10,000 45.5 4 5 . 6 I-PO.o(M 48.3' 47.8 1-30,OoU 10 3 1-10,000 66.1 56 3 1 -?O.(HHJ 56.8 a6.7 1 40.000 44.4 t34.8 40.6 38.5
m.5 34.7
44 1
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