A New Synthesis and Confirmation of the Structure ... - ACS Publications

SYNTHESIS AND CONF:[RMATION OF STRUCTURE OF AMIDONE

Dec., 19-17

member, oxidized to the corresponding sulfone series. Preliminary testing indicates that the com~~

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pounds are inactive against electrically induced convulsions. DETROIT,MICHIGAN

RECEIVED MAY14, 1947

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RESEARCH LABORATORIES OF J . T. BAKERCHEMICAL CO.]

A New Synthesis and Confirmation of the Structure of Amidonel BY NELSONR.EASTON, JOHbr H. GARDNER .4ND JOSEPH R. STEVENS The original procedure for the synthesis of the nitrile (IV). The hydrochloride of 3,3-diphenylnew German analgesic, Amidone or 10820,2in- S-methyltetrahydro-2-furanoneimine(I) gave the volves some technical difficulties due to the forina- satne lactone on long standing in aqueous solution of isomeric aminonitriles in approximately tion. These facts can only be accounted for by a equal a m o ~ n t s . A ~ new synthesis which avoids straight chain structure for the aminonitrile (IV). this difficulty has been developed. (CsHdzC-CN (C~HFJ~C-CN Diphenylacetonitrile was condensed with proI I CH=CHCHa CHzCH=CHz pylene oxide in the presence of sodium amide to yield 3,3-diphenyl-5-methyltetrahydro-2-furanoneimine (I),which was isolated as the hydroclilosteps (C6H.j)zC-C=0 ride. On treating this compound with phosphorus ' O +I.HCI tribromide, 4-bromo-2,2-diphenylpentanenitrileI V -----+/ CHz-CHCHj (11) was formed. The analogous chlorine comVI1 pound (111) was prepared in a similar manner. Either of these halonitriles, condensed with diExperimental methylamine, gave 4-dimethylamino-2,2-dipheriyl3,3-Diphenyl-S-methyltetrahydro-Z-furanoneimine pentanenitrile ( IV), from which Amidone was pre- Hydrochloride (I) .-To a well-stirred suspension of 20 g. pared by the action of ethylmagnesium bromide, of sodium amide in 100 ml. of benzene there was added 96 g. of diphenylacetonitrile. The mixture was heated t," a s in the original synthesis.2

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40-45' for one and a half hours and then cooled to 20 29 g. of propylene oxjde then was added, with the temperature kept a t 20-25 . The mixture was then boiled for I '>o CHaCHXCHa fifteen minutes and poured into a large excess of water. The benzene layer was separated and dried over magnesium CH?--