CH314561A - Process for the preparation of m-guanidino-m'-amidino-diazoaminobenzene diacetate - Google Patents
Process for the preparation of m-guanidino-m'-amidino-diazoaminobenzene diacetateInfo
- Publication number
- CH314561A CH314561A CH314561DA CH314561A CH 314561 A CH314561 A CH 314561A CH 314561D A CH314561D A CH 314561DA CH 314561 A CH314561 A CH 314561A
- Authority
- CH
- Switzerland
- Prior art keywords
- guanidino
- amidino
- diacetate
- diazoaminobenzene
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- PHXHYPQRDRRSAN-UHFFFAOYSA-N 3-aminobenzenecarboximidamide;hydrochloride Chemical compound Cl.NC(=N)C1=CC=CC(N)=C1 PHXHYPQRDRRSAN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- JJDYAJYFQDEUGM-UHFFFAOYSA-M [Cl-].N(C(=N)N)C=1C=C(C=CC=1)[N+]#N Chemical compound [Cl-].N(C(=N)N)C=1C=C(C=CC=1)[N+]#N JJDYAJYFQDEUGM-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- XYSWGAAAYXKWOW-UHFFFAOYSA-N 2-(3-aminophenyl)guanidine Chemical compound NC(=N)NC1=CC=CC(N)=C1 XYSWGAAAYXKWOW-UHFFFAOYSA-N 0.000 description 1
- 241000223836 Babesia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 201000008680 babesiosis Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- -1 m-acetaminophenylguanidine carbonate Chemical compound 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung von m-Guanidino-m'-amidino-diazoaminobenzol-diacetat Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung von m-Guanidino - m'- amidino - diazoamino -benzol- diaeetat, das dadurch gekennzeichnet ist, dass man m-(Tuanidino-plienyldiazoniumchlorid mit ni-Amino-benzamidinhydrochlorid in schwach saurer Lösung umsetzt und das Dihydrochlo- rid über das Carbonat in das Diacetat über führt.
Das Verfahrensprodukt stellt ein schwach gelbes Pulver dar, das nach Umkristallisieren aus Methanol und Aceton bei 173 unter Zer setzung schmilzt. Es zeichnet sich durch her vorragende Wirksamkeit gegen Blutparasiten, z. B. Trypanosomen, Babesien u. a., aus. Beispiel
EMI0001.0018
25 g m-Acetamino-phenylguanidincarbonat (F. 118 ) werden durch einstündiges Erwär men mit 160 cm-' Wasser und 40 cms konzen trierter Salzsäure im Wasserbad verseift.
Die erhaltene Lösung des salzsauren m-Amino- phenylguanidins wird mit 7 g Natriumnitrit diazotiert und mit einer Lösung von 23 g m-Aminobenzamidin-hydrochlorid unter Eis kühlung vermischt.
Man fügt etwa 100 cm3 gesättigte Natriumacetatlösung und sehr viel gesättigte Natriumchloridlösung hinzu, wobei sieh allmählich: das gelbliche, sehr voluminöse Dibydroehlorid des m-Gua.nidino-m'-amidino- diazoaminobenzols ausscheidet, das abgesaugt und mit verdünnter Natriumchloridlösung ge waschen wird.
Es wird durch Verrühren mit Sodalösung in das graugelbe Carbonat über geführt, das nach dem Umkristallisieren aus Wasser bei 94 unter Zersetzung schmilzt. Beim Ansäuern in Methanol mit Eisessig geht es unter Kohlensäüreentwicklung in Lösung, aus der durch Zusatz von Äther das Diacetat gefällt wird, das beim Verrühren mit Aceton fest wird und nach dem Umkristallisieren aus Methanol und Aceton ein schwach gelbes Pulver bildet. F. 173 unter Zersetzung. Es löst sich leicht. mit goldgelber Farbe in Was ser.
Natronlauge fällt aus der Lösung die braunrote Base, die beim Verreiben mit Was ser allmählich fest wird.
Process for the preparation of m-guanidino-m'-amidino-diazoaminobenzene diacetate The subject of the present additional patent is a process for the preparation of m-guanidino - m'-amidino - diazoamino-benzene diaetate, which is characterized in that one m - (Tuanidino-plienyldiazonium chloride is reacted with ni-amino-benzamidine hydrochloride in a weakly acidic solution and the dihydrochloride is converted into the diacetate via the carbonate.
The process product is a pale yellow powder which, after recrystallization from methanol and acetone, melts at 173 with decomposition. It is characterized by its excellent effectiveness against blood parasites, e.g. B. Trypanosomes, Babesia u. a., off. example
EMI0001.0018
25 g of m-acetaminophenylguanidine carbonate (F. 118) are saponified by heating for one hour with 160 cm- 'water and 40 cms of concentrated hydrochloric acid in a water bath.
The resulting solution of hydrochloric acid m-aminophenylguanidine is diazotized with 7 g of sodium nitrite and mixed with a solution of 23 g of m-aminobenzamidine hydrochloride while cooling with ice.
About 100 cm3 of saturated sodium acetate solution and a great deal of saturated sodium chloride solution are added, and you gradually see: the yellowish, very voluminous dibydrochloride of m-gua.nidino-m'-amidino-diazoaminobenzene separates, which is filtered off with suction and washed with dilute sodium chloride solution.
It is converted into the gray-yellow carbonate by stirring with soda solution, which, after recrystallization from water, melts at 94 ° C with decomposition. When acidifying in methanol with glacial acetic acid, it goes into solution with evolution of carbonic acid, from which the diacetate is precipitated by adding ether, which solidifies when stirred with acetone and forms a pale yellow powder after recrystallization from methanol and acetone. F. 173 with decomposition. It comes off easily. with golden yellow color in water.
Sodium hydroxide solution precipitates the brown-red base, which gradually solidifies when rubbed with water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE314561X | 1951-05-21 | ||
| CH306506T | 1952-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314561A true CH314561A (en) | 1956-06-15 |
Family
ID=25735170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314561D CH314561A (en) | 1951-05-21 | 1952-05-19 | Process for the preparation of m-guanidino-m'-amidino-diazoaminobenzene diacetate |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314561A (en) |
-
1952
- 1952-05-19 CH CH314561D patent/CH314561A/en unknown
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