Patent GB-819587-A (GB)
Title: Bis-amidinohydrazones
Inventor: BIRTWELL STANLEY
IPC: C07C281/18
Filed: 1956-06-15
Abstract: The invention comprises bis-amidinohydrazones of the general formula <F\1> and their acid addition salts (wherein R1 is a hydrocarbon radical which may optionally be substituted, R2, R3, R4, R5 and R6 are hydrogen atoms or alkyl radicals, each containing not more than 3 carbon atoms, and X is a direct link, a polymethylene radical -(CH2)nin which n is 1 to 4, a vinylene radical -CH=CH-, or a p-phenylene radical), and their preparation by reacting an aminoguanidine of the general formula <FORM:0819587/IV (b)/1> (or an acid addition salt thereof) with a dicarbonyl compound of the formula R5CO-X-COR6 or a functional derivative (e.g. a bisulphite compound), thereof.  The aminoguanidine starting materials are prepared, for example, by reacting an S-alkyl or S-aralkyl-isothiourea with the appropriate hydrazine derivative.  Examples describe the preparation by the above method, of the following compounds: 1 : 2 - bis - p - chlorophenylamidinohydrazonoethane, 2 : 3 - bis - p - chlorophenylamidinohydrazonobutane dihydrochloride, 1 : 2-bis-p - chlorophenylamidinohydrazonopropane dihydrochloride, 2 : 3 - bis - p - bromophenylamidinohydrazonobutane dihydriodide, 2 : 3-bis - 31 : 41 - dichlorophenylamidinohydrazonopropane dihydrochloride, 2 : 3 - bis - 31 : 41-dichlorophenylamidinohydrazonobutane dihydrochloride, 2 : 3 - bis - phenylamidinohydrazonobutane dihydrochloride, 1 : 2-bis-phenylamidinohydrazonoethane:dihydrochloride, 1:2-bis - benzylamidinohydrazonoethane dihydriodide, 1 : 2 - bis - p - methoxyphenylamidinohydrazonoethane dihydriodide, 1 : 2 - bis - p-fluorophenylamidinohydrazonoethane dihydriodide, 2 : 3 - bis - p - fluorophenylamidinohydrazonobutane dihydriodide, 2 : 3 - bis - p-tolylamidinohydrazonobutane dihydrochloride, 1 : 2 - bis - m - tolylamidinohydrazonopropane dihydriodide, 1 : 2 - bis - 21 : 51 - dimethylphenylamidinohydrazonoethane dihydriodide, 2 : 3 - bis - 31 : 41 - dimethylphenylamidinohydrazonobutane dihydriodide, 1 : 2 - bis - 21 : 31-dimethylphenylamidinohydrazonoethane dihydriodide, 2 : 5 - bis - p - chlorophenyl - amidinohydrazonohexane dihydrochloride, 1 : 4-bis - p - tolylamidinohydrazonomethylbenzene dihydrochloride, 1 : 4 - bis - isopropylamidinohydrazonomethylbenzene dihydrobromide, 1 : 4-bis - p - chlorophenylamidinohydrazonomethylbenzene dihydrochloride, 1 : 2-bis-21 : 41 : 51-trimethylphenylamidinohydrazonoethane dihydriodide, 2 : 3 - bis - 21 : 41 - dimethyl - phenylamidinohydrazonopropane, 1 : 2 - bis - N - p - chlorophenyl - N : N1 - dimethylamidinohydrazonoethane dihydrochloride, 1 : 2 - bis - N - p - chlorophenyl - N1 - isopropylamidinohydrazonoethane dihydrochloride, 1 : 2 - bis-p - nitrophenylamidinohydrazonoethane dihydrochloride, 2 : 3 - bis - cyclohexylamidinohydrazonobutane dihydrochloride, 1 : 2-bis-p-hydroxyphenylamidinohydrazonoethane dihydriodide, 2 : 3 - bis - p - methylsulphonyl - phenylamidinohydrazonobutane dihydriodide, 1 : 2 - bis - a  - naphthylamidinohydrazonoethane, 1 : 2 - bis - b  - naphthylamidinohydrazonoethane, 1 : 2 - bis - N1 : N1 - dimethyl-N2 - phenylamidinohydrazonoethane dihydriodide, 1 : 2 - bis - p - ethoxyphenylamidinohydrazonoethane dihydrochloride, and 1 : 6-bis - p - chlorophenylamidinohydrazonohexane. 1 : 4 - Bis - p - chlorophenylamidinohydrazonobut-2-ene dihydrochloride is prepared by the action of N1-amino-N2-p-chlorophenylguanidine hydrochloride in water on 2 : 5-diethoxy-2 : 5-dihydrofuran without isolation of the intermediate dicarbonyl compound.  N1 - Amino - N2 - p - chlorophenylguanidine hydrochloride is prepared by reacting aqueous hydrazine monohydrochloride with N-p-chlorophenyl-S-methyl-isothiourea.  The Provisional Specification also relates to bis-amidinohydrazones of the general formula above in which R2, R3, R4, R5 and R6 represent hydrogen or hydrocarbon radicals, optionally substituted, and X is a "bridging group," but in which, of R1, R2, R3, R5 and R6, at least one is or contains an aryl nucleus bearing at least one halogen or alkoxy substituent. Specification 800,869 is referred to.