CH231013A - Process for the preparation of 4,4'-diamidino-a, e-diphenoxypentane. - Google Patents
Process for the preparation of 4,4'-diamidino-a, e-diphenoxypentane.Info
- Publication number
- CH231013A CH231013A CH231013DA CH231013A CH 231013 A CH231013 A CH 231013A CH 231013D A CH231013D A CH 231013DA CH 231013 A CH231013 A CH 231013A
- Authority
- CH
- Switzerland
- Prior art keywords
- diphenoxypentane
- anhydrous
- preparation
- hydrogen halide
- converted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 2
- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- -1 ethylimino ether hydrochloride Chemical compound 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von 4,4'-Diamidino-a"e-diphenogypentan. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung von 4,4'-Di- amidino-a, e-diphenoxypentan, dadurch ge kennzeichnet, dass man 4,4'-Dicyan-a, e-di- phenoxypentan in absolut alkoholischer Lö sung mit wasserfreiem Halogenwasserstoff be handelt und das entstandene Iminoätherhydro- halogenid mit Ammoniak in das Diamidin überführt.
Die neue Verbindung schmilzt bei 186 bis<B>1871</B> C unter Zersetzung. Sie lässt sich leicht in ihr bei<B>2360</B> C schmelzendes Dihydro- chlorid oder in andere Salze überführen und kann sowohl als solche als auch in Form ihrer Salze als Arzneimittel verwendet werden.
Als Halogenwasserstoff verwendet man mit Vorteil trockenes Chlor- oder Bromwas-. serstoffgas. Neben dem absoluten Alkohol kann die Reaktionslösung auch noch weitere wasserfreie Lösungsmittel, wie Nitrobenzol, Chloroform usw., enthalten.
Die Ammoniak behandlung erfolgt zweckmässig mit einer alkoholischen Ammoniaklösung. <I>Beispiel:</I> 2,5 g 4,4'-Dicyan-a, e-diphenoxypentan (er halten durch Reaktion zwischen p-Oxybenzo- nitril und Pentainethylendibromid in wässri ger alkalischer Lösung, Schmelzpunkt 114" C) werden in 15 cmif Nitrobenzol aufgelöst und 2,5 cm' absoluten Äthylalkohols zugegeben. Die Lösung wird mit trockenem Chlorwasser stoffsäuregas bei<B>00</B> C gesättigt und 48 Stun den stehengelassen.
Sie wird dann mit trocke nem Äther verdünnt und das abgeschiedene 4,4'-Di(äthyliminoätherhydrochlorid) des a, s- Diphenoxypentans wird filtriert und mit Äther gewaschen. 4 g dieser Verbindung werden mit 30 cm' 6o/oiger äthylalkoholischer Am moniaklösung gemischt und in einem ge schlossenen Gefäss 5 Stunden lang auf 500 erhitzt.
Der Alkohol wird entfernt und das zurückbleibende p,p'-Diamidin-a, e-diphenoxy- pentan vom Schmelzpunkt 186-187o C (unter Zersetzung) zweckmässig zweimal aus ver dünnter Salzsäure umkristallisiert, wonach man das Dihydrochlorid durch Auflösen in Wasser und Abscheiden mit Aceton isolieren kann. Letzteres schmilzt bei 236"C.
Process for the preparation of 4,4'-diamidino-a "e-diphenogypentane. The subject of the present patent is a process for the preparation of 4,4'-diamidino-a, e-diphenoxypentane, characterized in that 4, 4'-Dicyan-a, e-diphenoxypentane in absolutely alcoholic solution is treated with anhydrous hydrogen halide and the resulting imino ether hydrohalide is converted into the diamidine with ammonia.
The new compound melts at 186 to <B> 1871 </B> C with decomposition. It can easily be converted into its dihydrochloride, which melts at <B> 2360 </B> C, or into other salts and can be used both as such and in the form of its salts as a medicinal product.
The hydrogen halide used is advantageously dry chlorine or bromine. hydrogen gas. In addition to the absolute alcohol, the reaction solution can also contain other anhydrous solvents such as nitrobenzene, chloroform, etc.
The ammonia treatment is best carried out with an alcoholic ammonia solution. <I> Example: </I> 2.5 g of 4,4'-dicyano-a, e-diphenoxypentane (obtained by reaction between p-oxybenzonitrile and pentainethylene dibromide in an aqueous alkaline solution, melting point 114 ° C.) Dissolved in 15 cm of nitrobenzene and 2.5 cm of absolute ethyl alcohol added. The solution is saturated with dry hydrochloric acid gas at <B> 00 </B> C and left to stand for 48 hours.
It is then diluted with dry ether and the deposited 4,4'-di (ethylimino ether hydrochloride) of a, s-diphenoxypentane is filtered and washed with ether. 4 g of this compound are mixed with 30 cm '6o / oiger ethyl alcoholic ammonia solution and heated to 500 in a closed vessel for 5 hours.
The alcohol is removed and the remaining p, p'-diamidine-a, e-diphenoxypentane with a melting point of 186-187o C (with decomposition) conveniently recrystallized twice from dilute hydrochloric acid, after which the dihydrochloride is dissolved by dissolving in water and separating with Can isolate acetone. The latter melts at 236 "C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE231013X | 1938-04-14 | ||
| CH214041T | 1938-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH231013A true CH231013A (en) | 1944-02-15 |
Family
ID=25725533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH231013D CH231013A (en) | 1938-04-14 | 1938-12-06 | Process for the preparation of 4,4'-diamidino-a, e-diphenoxypentane. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH231013A (en) |
-
1938
- 1938-12-06 CH CH231013D patent/CH231013A/en unknown
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