PL8058B1 - The method of obtaining symmetrical! of the diarylguanidines. - Google Patents

The method of obtaining symmetrical! of the diarylguanidines. Download PDF

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Publication number
PL8058B1
PL8058B1 PL8058A PL805826A PL8058B1 PL 8058 B1 PL8058 B1 PL 8058B1 PL 8058 A PL8058 A PL 8058A PL 805826 A PL805826 A PL 805826A PL 8058 B1 PL8058 B1 PL 8058B1
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PL
Poland
Prior art keywords
diarylguanidines
guanidine
symmetrical
aryl
obtaining symmetrical
Prior art date
Application number
PL8058A
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Polish (pl)
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Application filed filed Critical
Publication of PL8058B1 publication Critical patent/PL8058B1/en

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Description

Jezeli arylo-ajminy wziete w nadmiarze poddac dzialaniu soli izojtio-moczniko-ete- róiw1, to otnzyma sie d|wu-arylowana guani¬ dyne. Przyteitn drugi substytuent nie przy¬ lacza sie do atomu azotu, z którym to ato¬ mem wia|ze sie pierwszy, lecz laczy sie z druga piemwiszorzedowa grupa aminowa guanidyny.Otrzymane w ten sposób zwiazki szcze¬ gólnie pod postacia ich soli, latwo rozpu¬ szczalnych w wodzie, posiadaja zastoso¬ wanie terapeutyczne; Przyklad I. 80 g aniliny ogrzewa sie z 72 g bromowoidorku S-etylo-izo-tiio-moczniika (lub tez jodo-wodorku S-metylo4zo-tio- mocznika, luib chlorowodorku S-benzioylo- izo-lio-mocznóka i tern podobnych, w odpo¬ wiadajacych siteohjometrycznyich ilosciach).Ogrzewanie profwadlzi sie w temperaturze 100—130°, w obecnosci malej ilosci wody, tak dlugo, az przestanie oddesitylowywac merkaptan, Produkt reakcji uwalnia sie od nadmiaru aniliny, przez /wyekstrahowanie jej eterem; osad alkalizuje ®ie lugiem so¬ dowym. Symetrycznie podstawiona dwu- fenylo-guanidyna krystalizuje sie wtedy pod postacia pryizm, bardzo trudno rozpu¬ szczalnych w wodzie, latwo natomiast, roz- pusizczaja)cycih sie w alkoholu i eterze.Zwiazek ten posiada punkt topnienia 148— 149°.Przyklad II. 10,8 g bromo-iwiodlorku S- etylo-izo-itio-mocznika ogrzewa sie w po¬ wyzej opisany sposób z 9-dioma gramamio-anizydyny. Powstaje azerwonawo-bru- natna masa, która uwalnia sie od nadmiaru o-anizydyny zapornoca eteru lub benzolu.Otrzymany, symetryczny bromowodorek dwu-f o-metoksy-f enylo) -guanidyny topi sie po przekrystalizowaniu z aicetonu lub alko¬ holu przy 195—196°. Z wodnego roztworu, wytraca sie zasade zapomoca traktowania alkaljamii, pod postacia oleju, który po pewnym czasie zestala sie. Zasada, tworza¬ ca biale, tluste blyszczace luski, topniejace przy 120° C, jest bardzo trudno rozpu¬ szczalna w wodizie, latwo rozpuszcza sie natomiast w rozpuszczalnikach organicz¬ nych. Przy gotowaniu z alkaljami tworzy odpowiedni mocznik. PL PLIf the arylamine taken in excess is treated with the isoitio-urea-ether salt, it becomes dvu-arylated guanidine. The confined second substitute does not attach to the nitrogen atom with which the first is linked, but connects to the second quadrate amino group of guanidine. The compounds thus obtained, especially in the form of their salts, are easily dissolved. water-soluble, have therapeutic use; Example I. 80 g of aniline is heated with 72 g of S-ethyl-iso-thiourea bromide (or also S-methyl-4-azo-thiourea-iodohydride, or S-benzioyl-iso-urea hydrochloride and the like, in corresponding siteohiometric amounts). The heating is carried out at a temperature of 100-130 ° in the presence of a small amount of water, until it ceases to evaporate the mercaptan. The reaction product is freed from excess aniline by / extracting it with ether; the precipitate is made alkaline with sodium liquor. The symmetrically substituted diphenyl-guanidine then crystallizes in the form of prism, which is very sparingly soluble in water, but readily dissolves in alcohol and ether. This compound has a melting point of 148-149 °. Example II. 10.8 g of S-ethyl-iso-thio-urea bromo-dihydrochloride are heated in the manner described above with 9-dioma-anisidine. A reddish-brown mass is formed, which is freed from the excess o-anisidine in the absence of ether or benzol. The resulting symmetrical di-methoxy-phenyl) -guanidine hydrobromide melts after recrystallization from aicetone or alcohol alcohol at 195 ° C. 196 °. From the aqueous solution, the principle is precipitated by an alkaline treatment in the form of an oil which solidifies over time. The base, which forms white, greasy, shiny scales, melting at 120 ° C, is very difficult to dissolve in water, but dissolves easily in organic solvents. When cooking with alkalis it forms the appropriate urea. PL PL

Claims (1)

Zastrzezenie patentowe.Patent claim. 1. Sposób otrzymywania symetrycznej dwu-arylo-guanidyny, wzglednie jej soli, znamienny tern, ze arylo-amcny, wziete w nadmiarze poddaje sie dzialaniu soli izo- tio-mocziniko-eterów. Chemische Fabrik auf Actien (vornt E. Schering). Zastepca: Inz. Cz. Raczynski, rzecznik patentowy. Druk L. Boguslawskiego, Warszawa. PL PLA method for the preparation of a symmetrical di-aryl-guanidine or its salt, characterized by the fact that aryl-ammonium is excessively treated with isothio-uine-ether salts. Chemische Fabrik auf Actien (vornt E. Schering). Deputy: Inz. Th. Raczynski, patent attorney. Printed by L. Boguslawski, Warsaw. PL PL
PL8058A 1926-11-16 The method of obtaining symmetrical! of the diarylguanidines. PL8058B1 (en)

Publications (1)

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PL8058B1 true PL8058B1 (en) 1927-12-31

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