Process for the manufacture of mono-(1,2-diarylamino-ethane)-derivatives of dicarbonyl compounds

摘要

Mono-(1,2-diarylaminoethane)-derivatives of a ,b - or a ,g -dicarbonyl compounds are obtained by heating a compound of the formula in which R1 is a phenyl or alkoxyphenyl radical, with an aldehyde of the formula OHC-R2 or a ketone of the formula R3-CH2-CO-R2 in which R2 is a phenyl, alkoxyphenyl, halogenphenyl, nitrophenyl or furoyl radical or together with R3 the divalent tetramethylene or o-methylene-phenyl radical, in which the benzene ring is directly attached to the carbonyl group, R3 otherwise being a hydrogen atom, in the absence of oxygen and moisture and, if desired, in a solvent which is inert with respect to the reactants. Reaction with the specified aldehydes provides products having the formula while the specified ketones give products having the formula in which R1, R2 and R3 have the meanings given above. Examples describe the preparation of 1,3 - diphenyl - 2 - benzoyl - imidazolidine, 1,3 - diphenyl - 2 - p - methoxybenzoyl - imidazolidine, 1,3 - diphenyl - 2 - p - chlorobenzoyl - imidazolidine and the corresponding bromo- and iodo-compounds, 1,3-diphenyl-2-m-nitrobenzoyl - imidazolidine, 1,3 - diphenyl - 2 - furoyl - imidazolidine, 1,3 - di - p - methoxyphenyl - 2 - furoyl - imidazolidine, 1,3 - di - p - methoxyphenyl - 2 - benzoyl - imidazolidine, the 1,2 - dianilinoethane derivative of 2-formyl-cyclohexanone-(1) (non-heterocyclic form), the 1,2-dianilinoethane derivative of 1-phenyl-1,3-dioxo-propane (non-heterocyclic form) and the 1,2-dianilinoethane derivative of 2-formyl-hydrindone-(1) (non-heterocyclic form). The bis-imidazolidinylidene reactants can be obtained by heating a compound of the formula R1-NH-CH2-CH2-NH-R1, in which R1 has the meaning given above, with an orthoformic acid alkyl ester in the absence of oxygen. For example, bis-[1,3-diphenylimidazolidinylidene-(2)] is obtained by heating 1,2-dianilinoethane with ethyl orthoformate in an atmosphere of nitrogen; in contact with solvents, the product is rapidly oxidized to 1,3-diphenylimidazolidone-(2).