CH314560A - Process for the preparation of di- (m, p'-guanidino) -diazoaminobenzene dihydrochloride - Google Patents
Process for the preparation of di- (m, p'-guanidino) -diazoaminobenzene dihydrochlorideInfo
- Publication number
- CH314560A CH314560A CH314560DA CH314560A CH 314560 A CH314560 A CH 314560A CH 314560D A CH314560D A CH 314560DA CH 314560 A CH314560 A CH 314560A
- Authority
- CH
- Switzerland
- Prior art keywords
- guanidino
- dihydrochloride
- diazoaminobenzene
- preparation
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 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 description 2
- 239000003929 acidic solution Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- -1 diazoaminobenzene dihydrochloride Chemical compound 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- XYSWGAAAYXKWOW-UHFFFAOYSA-N 2-(3-aminophenyl)guanidine Chemical compound NC(=N)NC1=CC=CC(N)=C1 XYSWGAAAYXKWOW-UHFFFAOYSA-N 0.000 description 1
- HXKWSIPCTVYMBN-UHFFFAOYSA-N 2-(4-aminophenyl)guanidine Chemical compound NC(=N)NC1=CC=C(N)C=C1 HXKWSIPCTVYMBN-UHFFFAOYSA-N 0.000 description 1
- JVRYXXSPGCUCIV-UHFFFAOYSA-N 2-(4-aminophenyl)guanidine;hydrochloride Chemical compound Cl.NC(=N)NC1=CC=C(N)C=C1 JVRYXXSPGCUCIV-UHFFFAOYSA-N 0.000 description 1
- 241000223836 Babesia Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- 201000008680 babesiosis Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Di-(m,p'-guanidino)-diazoaminobenzol-dihydrochlorid Das Verfahrensprodukt stellt ein gelbliches Pulver dar, das nach Umkristallisieren aus Methanol und Aceton bei 185 -unter Zerset zung schmilzt. Es zeichnet sich durch hervor ragende Wirksamkeit gegen Blutparasiten, z. B. Trvpanosomen, Babesien u. a., aus.
<I>Beispiel</I> Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Herstellung von Di- (m,p'-guanidino) - diazoaminoben7ol-dihydro- ehlorid, das dadurch gekennzeichnet ist, dass man m-Guanidino-phenyldiazoniumchlorid in sehwach saurer Lösung mit p-Amino-phenyl- guanidin-hyclrochlorid umsetzt.
EMI0001.0016
25 g m-Acetamino-phenylguanidincarbonat (F. 118 ) werden durch einstündiges Erwär men mit 160 ein- Wasser und 40 cm3 konzen trierter Salzsäure im Wasserbad verseift. Die erhaltene Lösung des salzsauren m-Amino- phenylguanidins wird mit 7 g Natriumnitrit dianotiert und mit einer Lösung von salzsau rem p-Amino-phenylguanidin aus 25 g p-Acet- amino-phenylguanidin-carbonat vermischt.
Auf Zusatz von überschüssiger gesättigter Na triumchloridlösung und etwa 1.00 em3 gesät tigter Natriumacetatlösung zu der eiskalten Mischung bildet sieh ein lehmgelber Brei, der naeh einiger Zeit abgesaugt und mit verdünn ter Kochsalzlösung, wenig eiskaltem Wasser und Aceton gewaschen wird. Nach dem Um kristallisieren aus Methanol und Aceton erhält man ein gelbes Pulver, das das Dihydrochlo- rid des Di-(m,p'-gtianidino)-diazoaminobenzols darstellt. F. 185 unter Zersetzung. Es ist leicht löslich in Wasser.
Durch Behandeln mit Sodalösung erhält man ein harzartiges Carbonat, das beim Rei ben fest wird und, aus Wasser umkristalli siert, ein graugelbes Pulver vom F. 149-150 unter langsamer Zersetzung darstellt.
Process for the preparation of di- (m, p'-guanidino) diazoaminobenzene dihydrochloride The process product is a yellowish powder which, after recrystallization from methanol and acetone at 185 °, melts with decomposition. It is characterized by its excellent effectiveness against blood parasites, e.g. B. Trvpanosomes, Babesia u. a., off.
<I> Example </I> The subject matter of the present additional patent is a process for the preparation of di- (m, p'-guanidino) - diazoaminoben7ol-dihydrochloride, which is characterized in that m-guanidino-phenyldiazonium chloride is used in a very weak state acidic solution with p-amino-phenyl-guanidine-hydrochloride.
EMI0001.0016
25 g of m-acetaminophenylguanidine carbonate (F. 118) are saponified by heating for one hour with 160 one-piece water and 40 cm3 of concentrated hydrochloric acid in a water bath. The resulting solution of hydrochloric acid m-aminophenylguanidine is dianotized with 7 g of sodium nitrite and mixed with a solution of hydrochloric acid rem p-aminophenylguanidine from 25 g of p-acetaminophenylguanidine carbonate.
When excess saturated sodium chloride solution and about 1.00 em3 saturated sodium acetate solution are added to the ice-cold mixture, a clay-yellow pulp is formed, which is sucked off after a while and washed with dilute sodium chloride solution, a little ice-cold water and acetone. After recrystallization from methanol and acetone, a yellow powder is obtained which is the dihydrochloride of di- (m, p'-gtianidino) -diazoaminobenzene. F. 185 with decomposition. It is easily soluble in water.
By treating with soda solution, a resinous carbonate is obtained, which solidifies on Rei ben and, recrystallized from water, is a gray-yellow powder of F. 149-150 with slow decomposition.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE314560X | 1951-05-21 | ||
| CH306506T | 1952-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314560A true CH314560A (en) | 1956-06-15 |
Family
ID=25735169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314560D CH314560A (en) | 1951-05-21 | 1952-05-19 | Process for the preparation of di- (m, p'-guanidino) -diazoaminobenzene dihydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314560A (en) |
-
1952
- 1952-05-19 CH CH314560D patent/CH314560A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH314560A (en) | Process for the preparation of di- (m, p'-guanidino) -diazoaminobenzene dihydrochloride | |
| DE637385C (en) | Process for the preparation of 2, 4-dioxo-1, 3, 3-trialkyl- and -1, 3, 3, 6-tetraalkyltetrahydropyridines | |
| DE731524C (en) | Process for the preparation of 1, 5-dichloronaphthalene-4, 8-dicarboxylic acid | |
| DE507796C (en) | Manufacture of vanillin | |
| DE875361C (en) | Process for the preparation of oxyphenyl-serines | |
| DE845347C (en) | Process for the preparation of pyridine-mercury compounds | |
| DE693922C (en) | sulfonic acid amide | |
| DE686701C (en) | Process for the preparation of aryl-substituted ª † -amino-ª ‰ -oxybutyric acids | |
| CH314559A (en) | Process for the preparation of di- (p, m'-amidino) -diazoaminobenzene dihydrochloride | |
| DE858697C (en) | Process for the preparation of Dicarbonsaeuredimethylolamiden | |
| AT166702B (en) | Process for the preparation of new halogenated pyrimidyl mercaptocarboxylic acids and their derivatives | |
| AT133505B (en) | Process for the preparation of ω-Oxyacylaminobenzolarsin- or -stibinoxden or ω-Oxyacylaminobenzolarsin- or -stibinsäuren. | |
| CH261828A (en) | Process for the preparation of a substituted 2,4-diamino-1,3,5-triazine. | |
| CH314849A (en) | Process for the preparation of N-guanyl-N'-p-guanylphenyl-diacetyl-dihydrazone dihydrochloride | |
| CH311087A (en) | Process for the preparation of di (p-guanidino) diazoaminobenzene diacetate. | |
| DE1135910B (en) | Process for the preparation of 2,5-bis-methylaethyleneimino-hydroquinone | |
| CH311088A (en) | Process for the preparation of p'-amidino-p-guanidino-diazoaminobenzene dihydrochloride. | |
| CH314561A (en) | Process for the preparation of m-guanidino-m'-amidino-diazoaminobenzene diacetate | |
| CH222491A (en) | Process for the preparation of 3-acetoxybisnorcholanyl-acetoxymethyl-ketone. | |
| CH133686A (en) | Process for the preparation of 2-oxynaphthalene-3-carboxylic acid-4'-chlorophenylamide. | |
| CH412887A (en) | Process for the preparation of addition salts of 1-methyl-3- (di-2-thienylmethylene) piperidine | |
| CH105106A (en) | Process for the preparation of an alkoxyakridine. | |
| CH162658A (en) | Process for the preparation of the sodium salt of an arsenic complex compound of catechinaric acid. | |
| CH281595A (en) | Process for the preparation of a halogenated pyrimidyl-mercapto-carboxylic acid. | |
| CH311086A (en) | Process for the preparation of di- (m-amidino) -diazoaminobenzene dihydrochloride. |