DE2747551A1 - Benzimidazolyl-guanidine cpds. prodn. - by neutralisation of ortho-phenylenediamine cpds. with hydrochloric acid and reaction with dicyandiamide - Google Patents
Benzimidazolyl-guanidine cpds. prodn. - by neutralisation of ortho-phenylenediamine cpds. with hydrochloric acid and reaction with dicyandiamideInfo
- Publication number
- DE2747551A1 DE2747551A1 DE19772747551 DE2747551A DE2747551A1 DE 2747551 A1 DE2747551 A1 DE 2747551A1 DE 19772747551 DE19772747551 DE 19772747551 DE 2747551 A DE2747551 A DE 2747551A DE 2747551 A1 DE2747551 A1 DE 2747551A1
- Authority
- DE
- Germany
- Prior art keywords
- cpds
- dicyandiamide
- phenylenediamine
- hydrochloric acid
- benzimidazolylguanidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 title claims abstract description 13
- JJWCTKUQWXYIIU-UHFFFAOYSA-N 2-Benzimidazolylguanidine Chemical compound C1=CC=C2NC(N=C(N)N)=NC2=C1 JJWCTKUQWXYIIU-UHFFFAOYSA-N 0.000 title claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 18
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 title abstract description 5
- 238000006386 neutralization reaction Methods 0.000 title abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000012452 mother liquor Substances 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 10
- -1 methoxy, phenyl Chemical group 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- IFYPQHGXCVZZMW-UHFFFAOYSA-N 2-(6-chloro-1h-benzimidazol-2-yl)guanidine Chemical compound C1=C(Cl)C=C2NC(N=C(N)N)=NC2=C1 IFYPQHGXCVZZMW-UHFFFAOYSA-N 0.000 description 1
- NFVKSWJIGKATLV-UHFFFAOYSA-N 2-(6-methyl-1h-benzimidazol-2-yl)guanidine Chemical compound CC1=CC=C2N=C(N=C(N)N)NC2=C1 NFVKSWJIGKATLV-UHFFFAOYSA-N 0.000 description 1
- NAGIDXZSUSERRK-UHFFFAOYSA-N 2-(6-nitro-1h-benzimidazol-2-yl)guanidine Chemical compound C1=C([N+]([O-])=O)C=C2NC(N=C(N)N)=NC2=C1 NAGIDXZSUSERRK-UHFFFAOYSA-N 0.000 description 1
- PBVBFKPJZFNFNY-UHFFFAOYSA-N 3,4-dichlorobenzene-1,2-diamine Chemical compound NC1=CC=C(Cl)C(Cl)=C1N PBVBFKPJZFNFNY-UHFFFAOYSA-N 0.000 description 1
- YWPGZWRHHRUXEK-UHFFFAOYSA-N 3,5-dichlorobenzene-1,2-diamine Chemical compound NC1=CC(Cl)=CC(Cl)=C1N YWPGZWRHHRUXEK-UHFFFAOYSA-N 0.000 description 1
- DMEPVFSJYHJGCD-UHFFFAOYSA-N 3,5-dimethylbenzene-1,2-diamine Chemical compound CC1=CC(C)=C(N)C(N)=C1 DMEPVFSJYHJGCD-UHFFFAOYSA-N 0.000 description 1
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
- WIHHVKUARKTSBU-UHFFFAOYSA-N 4-bromobenzene-1,2-diamine Chemical compound NC1=CC=C(Br)C=C1N WIHHVKUARKTSBU-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 description 1
- KYEFUIBOKLKQPD-UHFFFAOYSA-N 4-phenylbenzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1C1=CC=CC=C1 KYEFUIBOKLKQPD-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Verfahren zur Herstellung von Benzimidazolylguanidinverbin-Process for the preparation of Benzimidazolylguanidinverbin-
dungen (2-Guanidino-benzimidazole) Die Erfindung betrifft ein Verfahren zur Herstellung von Benzimidazolylguanidin und dessen im Benzolkern substituierte Verbindungen (2-Guanidino-benzimidazole) aus den entsprechenden bPhenylendiaminen und Dicyandiamid in wäßriger Lösung. dungen (2-guanidino-benzimidazole) The invention relates to a method for the production of benzimidazolylguanidine and its substituted in the benzene nucleus Compounds (2-guanidino-benzimidazoles) from the corresponding b-phenylenediamines and dicyandiamide in aqueous solution.
Es ist bekannt, Benzimidazolylguanidinverbindungen aus dem Dihydrochlorid von entsprechenden o-Phenylendiaminverbindungen herzustellen, wobei nach der Zugabe des Dicyandiamids zur wäßrigen Lösung der Dihydrochloride ein bis fünf Stunden am Rückfluß gekocht wird (Us-PS 3 023 103>; KING, FE. u. Mitarb. I.Chem.Soc. (London) 1948, 1366-71) Diese Verfahren haben insbesondere den Nachteil, daß die gesamte Neutralisationswärme bei der Isolierung der o-Phenylendiaminverbindungen verlorengeht. Außerdem sind solche o-Phenylendiaminverbindungen oft sehr empfindliche Verbindungen, die leicht zur Bildung verfärbter Nebenprodukte neigen, welche bei öfterer Handhabung verstärkt auftreten: hierdurch vermindert sich die Ausbeute an den gewünschten Benzimidazolylguanidinverbindungen.It is known that benzimidazolylguanidine compounds are obtained from the dihydrochloride of corresponding o-phenylenediamine compounds, after adding of the dicyandiamide to the aqueous solution of the dihydrochloride one to five hours on Reflux is boiled (US-PS 3 023 103>; KING, FE. And employees I. Chem. Soc. (London) 1948, 1366-71) These methods have the particular disadvantage that the total heat of neutralization in the isolation of the o-phenylenediamine compounds get lost. In addition, such o-phenylenediamine compounds are often very sensitive Compounds that are prone to the formation of discolored by-products, which at occur more frequently: this reduces the yield the desired benzimidazolylguanidine compounds.
Es bestand daher die Aufgabe, ein Verfahren zu finden, welches es gestatte'-, solche Benzimidazolylguanidinverbindungen in ernöhter Ausbeute, höherer Reinheit und vor allem energiesparender herzustellen.The task was therefore to find a method which would do it allow such benzimidazolylguanidine compounds in increased yield, higher To produce purity and, above all, more energy-efficient.
Diese Aufgabe des Verfahrens zur Herstellung von Benzimidazolylguanidinverbindungen der allgemeinen Formel I wobei R Chlor-, Brom- oder Wasserstoffatome sein können oder Methyl-, Methoxy-, Phenyl- oder Nitrogruppen darstellen, wurde dadurch gelöst, daß man in vorgelegte Salzsäure eine o-Phenylendiarninverbindung so rasch einträgt, daß sich die Mischung auf mindestens 60 OC erwärmt, zu dieser Mischung Dicyandiamid in einer solchen Geschwindigkeit zugibt, daß ohne Zufuhr äußerer Wärmeenergie eine Temperatur von 120 OC erreicht wird, anschließend durch Zugabe von Natronlauge die gebildete Benzimidazolylguanidinverbindung ausfällt, in an sich bekannter Weise von der Mutterlauge abtrennt, mit Wasser chloridfrei wäscht und anschließend trocknet.This object of the process for the preparation of benzimidazolylguanidine compounds of the general formula I. where R can be chlorine, bromine or hydrogen atoms or represent methyl, methoxy, phenyl or nitro groups, was solved by introducing an o-phenylenediarnine compound into hydrochloric acid so quickly that the mixture warms to at least 60.degree , adds dicyandiamide to this mixture at such a rate that a temperature of 120 ° C. is reached without the supply of external heat energy, then the benzimidazolylguanidine compound formed precipitates by adding sodium hydroxide solution, separated from the mother liquor in a manner known per se, washed free of chloride with water and then dries.
Nach dem Verfahren der Erfindung geht man also nicht von den Dihydrochloriden der o-Phenyldendiaminverbindungen aus, sondern von deren Basen selbst und benutzt die bei deren Eintragen in vorgelegte Salzsäure entstehende Neutralisationswärme zum Aufheizen auf die für das Anspringen der Reaktion des Dihydrochlorids mit Dicyandiamid erforderliche Starttemperatur. Hierbei überraschte, daß bei entsprechend schnellem Dicyandiamid-Eintrag die sich einstellende Reaktionstemperatur für eine restlose Umsetzung ausreicht und deswegen auf das anschließende RücX-flußkochen verzichtet werden kann. Als weitere bemerkenswerte Vorteile dieser erfindungsgemäßen Verfahrensweise ergaben sich gegenüber dem Stand der Technik verbesserte Ausbeuten und erhöhte Reinheit.The process of the invention therefore does not start with the dihydrochlorides of the o-phenyldiamine compounds, but separate from their bases themselves and uses the heat of neutralization that arises when it is introduced into the hydrochloric acid for heating up for starting the reaction of the dihydrochloride with dicyandiamide required starting temperature. It was surprising that with a correspondingly fast Dicyandiamide entry the resulting reaction temperature for a complete Implementation is sufficient and therefore the subsequent RücX river cooking is dispensed with can be. As further notable advantages of this procedure according to the invention The results were improved yields and increased purity compared to the prior art.
Demgemäß verläuft das Verfahren zur Herstellung von Benzimidazolylguanidinverbindungen gemäß Formel I in folgenden Schritten: 1. Eintragen des o-Phenylendiamins in Salzsäure unter Umrühren, wobei sich das Gemisch auf 60 bis 70 OC erwärmt.Accordingly, the process for the preparation of benzimidazolylguanidine compounds proceeds according to formula I in the following steps: 1. Enter the o-phenylenediamine in hydrochloric acid with stirring, the mixture warming to 60 to 70 ° C.
2. Eintragen von Dicyandiamid in das 70 OC warme Gemisch unter weiterem Umrühren derart, daß die Temperatur 120 OC nicht überschreitet.2. Adding dicyandiamide to the 70 ° C warm mixture, among other things Stir in such a way that the temperature does not exceed 120 ° C.
3. Zugabe von NaOH nach beendeter Reaktion zur Ausfällung der gebildeten Benzimidazolylguanidin verbindung.3. Addition of NaOH after the reaction has ended to precipitate the formed Benzimidazolylguanidine compound.
4. Abkühlen der Mischung, Abtrennen des Feststoffs von der Mutterlauge, Auswaschen bis zur Chloridfreiheit und anschliessendes Trocknen auf bekannte Weise.4. Cooling the mixture, separating the solid from the mother liquor, Wash out until it is free of chloride and then dry in a known manner.
Zur wärmewirtschaftlich günstigen Durchführung wird das Reaktionsgemisch bei den Schritten 1 und 2 von außen nicht oder nur unwesentlich erwärmt und Wärmeverluste von dem reagierenden Gemisch weitestgehend verhindert. Die Umsetzung wird somit vorzugsweise unter im wesentlichen adiabatischen Bedingungen durchgeführt.The reaction mixture is used for the heat-economically favorable implementation in steps 1 and 2 not or only insignificantly heated from the outside and heat losses largely prevented by the reacting mixture. The implementation is thus preferably carried out under essentially adiabatic conditions.
Das vorliegende Verfahren wird am günstigsten in einer Kombination von zwei Rührwerksbehältern durchgeführt, von denen der erste gut isoliert und heizbar, der zweite nicht isoliert und wassergekühlt ist.The present method is most beneficial in a combination carried out by two agitator tanks, the first of which is well insulated and heatable, the second is not insulated and water-cooled.
Zur näheren Erläuterung der Erfindung sollen die folgenden Beispiele dienen: Beispiel 1 In einen 1 200 Vol.-Teile fassenden Rührbehälter, der isoiiert und mit einem Ruckflußkühler versehen ist, werden 175 Gew.-Teile Salzsäure (29.3 %ig) sowie 10 Vol.-Teile Wasser aufgegeben und anschließend 77,2 Gew.-Teile o-Phenylendiamin eingetragen.The following examples are intended to explain the invention in greater detail serve: Example 1 In a stirred tank with a capacity of 1,200 parts by volume, which is isolated and is provided with a reflux condenser, 175 parts by weight of hydrochloric acid (29.3 %) and 10 parts by volume of water and then 77.2 parts by weight of o-phenylenediamine registered.
Nach dem Eintragen hat das Gemisch eine Temperatur von 68 OC Dann werden während 20 Minuten 60 Gew.-Teile Dicyandiamid eingetragen, wobei die Temperatur auf 122 OC ansteigt. Nach Beendigung des Eintragens und kurzzeitigem Nachrühren ( 5 bis 10 Minuten) wird durch Zugabe von Natronlauge (20 %ig) das gebildete Benzimidazolylguanidin in Freiheit gesetzt. Das entstandene Gemisch wird in einen R:ihrwerksbehälter abgelassen, auf Raumtemperatur abgekühlt und das ausgefallene Produkt abgeschleudert. Nach dem Auswaschen mit Wasser bis zur Chloridfreiheit wird das Produkt bei 90 bis 100 °C im Vakuum getrocknet.After entering the mixture has a temperature of 68 OC then 60 parts by weight of dicyandiamide are added over the course of 20 minutes, the temperature rises to 122 OC. After completing the entry and briefly stirring (5 to 10 minutes) the benzimidazolylguanidine is formed by adding sodium hydroxide solution (20%) set in freedom. The resulting mixture is drained into a R: your factory container, cooled to room temperature and the precipitated product spun off. After this The product is washed out with water until it is free of chloride at 90 to 100 ° C dried in vacuum.
Es werden 105 Gew.-Teile Produkt mit 39,9 % N und 0,4 % feuchtigkeit, entsprechend einer Ausbeute von 84 %, erhalten.There are 105 parts by weight of product with 39.9% N and 0.4% moisture, corresponding to a yield of 84%.
Beispiel 2 Entsprechend Beispiel 1 werden 175 Gew.-Teile Salzsäure (29,3 %ig) mit 10 Vol.-Teilen Wasser und 102,7 Gew.-Teilen 1,2-Diamino-5-Chlorbenzol vermischt. Das Gemisch erreicht eine TamP peratur von 60 bis 70 OC Anschließend werden innerhalb von 20 Minuten 60 Gew.-Teile Dicyandiamid eingetragen. Man verfährt weiter entsprechend Beispiel 1. Nach dem Trocknen erhält man 115 Gew.-Teile 5-Chlorbenzimidazolylguanidin mit 32,0 % N und 0,3 % H20, entsprechend einer Ausbeute von 76,5 %.Example 2 As in Example 1, 175 parts by weight of hydrochloric acid are used (29.3%) with 10 parts by volume of water and 102.7 parts by weight of 1,2-diamino-5-chlorobenzene mixed. The mixture then reaches a temperature of 60 to 70 OC 60 parts by weight of dicyandiamide are entered within 20 minutes. One moves Further as in Example 1. After drying, 115 parts by weight of 5-chlorobenzimidazolylguanidine are obtained with 32.0% N and 0.3% H20, corresponding to a yield of 76.5%.
Beispiel 3 Entsprechend Beispiel 1 werden 175 Gew.-Teile Salzsäure (29,3 %ig) mit 86 Gew.-Teilen 1,2-Diamino-5-methylbenzol und 60 Gew.-Teilen Dicyandiamid eingesetzt.Example 3 As in Example 1, 175 parts by weight of hydrochloric acid are used (29.3%) with 86 parts by weight of 1,2-diamino-5-methylbenzene and 60 parts by weight of dicyandiamide used.
Man erhält 106 Gew.-Teile 5-Methylbenzimidazolylguanidin mit 35,8 % N und 0,5 % H20, entsprechend einer Ausbeute von 80,0 %.106 parts by weight of 5-methylbenzimidazolylguanidine at 35.8 are obtained % N and 0.5% H20, corresponding to a yield of 80.0%.
Beispiel 4 Beim Einsatz von 175 Gew.-Te'ilen Salzsäure (29,3 %ig), 107 Gew.-Teilen 1,2-Diamino-5-nitrobenzol und 60 Gew.-Teilen Dicyandiamid entsprechend Beispiel 1 erhält man nach dem Trocknen 119 Gew.-Teile 5-Nitrobenzimidazolylguanidin mit 34,9 % N und 0,5 % H20. Die Ausbeute beträgt 78,0 %.Example 4 When using 175 parts by weight of hydrochloric acid (29.3%), 107 parts by weight of 1,2-diamino-5-nitrobenzene and 60 parts by weight of dicyandiamide accordingly Example 1 gives 119 parts by weight of 5-nitrobenzimidazolylguanidine after drying with 34.9% N and 0.5% H20. The yield is 78.0%.
Beispiel 5 - 11 In der in Beispiel 1 beschriebenen Weise werden die in der nachfolgenden Tabelle aufgeführten o-Phenylendiamine in die entsprechenden Benzimidazolylguanidinverbindungen übergeführt. Beispiel o-Phenylendiamin Benzimidazolyl- N-Gehalt Cl-Ge- Br-Ge- Ausbeu-Nr. guanidin (BIG) % halt % halt % te % 5 1,2-Diamino-4,6-dichlorbenzol 4,6-Dichlor-BIC 27,2 29,7 - 68 6 1,2-Diamino-5,6-dichlorbenzol 4,5-Dichlor-BIG 27,7 19,3 - 73 7 1,2-Diamino-4,5,6-trichlor- 4,5,6-Trichlor- 23,7 38,2 - 63 benzol BIG 8 1,2-Diamino-5-brombenzol 5-Brom-BIG 26,3 - 31,0 76 9 1,2-Diamino-4,6-dimethylbenzol 4,6-Dimethyl-BIG 33,2 - - 69 10 1,2-Diamino-4,6-mthoxybenzol 5-Methoxy-BIG 32,3 - - 58 11 1,2-Diamino-5-phenylbenzol 5-Phenyl-BIG 27,0 - - 77Examples 5-11 In the manner described in Example 1, the o-Phenylenediamines listed in the table below into the corresponding Benzimidazolylguanidinverbindungen transferred. Example o-phenylenediamine Benzimidazolyl-N content Cl-Ge Br-Ge Ausbeu no. guanidine (BIG)% hold% hold% te% 5 1,2-diamino-4,6-dichlorobenzene 4,6-dichloro-BIC 27.2 29.7 - 68 6 1,2-diamino-5,6-dichlorobenzene 4,5-dichloro-BIG 27.7 19.3-73 7 1,2-diamino-4,5,6-trichloro-4,5,6-trichloro-23.7 38.2-63 benzene BIG 8 1,2-diamino-5-bromobenzene 5-bromo-BIG 26.3-31.0 76 9 1,2-diamino-4,6-dimethylbenzene 4,6-dimethyl-BIG 33.2 - - 69 10 1,2-diamino-4,6-methoxybenzene 5-methoxy-BIG 32.3 - - 58 11 1,2-diamino-5-phenylbenzene 5-phenyl-BIG 27.0 - - 77
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772747551 DE2747551A1 (en) | 1977-10-22 | 1977-10-22 | Benzimidazolyl-guanidine cpds. prodn. - by neutralisation of ortho-phenylenediamine cpds. with hydrochloric acid and reaction with dicyandiamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772747551 DE2747551A1 (en) | 1977-10-22 | 1977-10-22 | Benzimidazolyl-guanidine cpds. prodn. - by neutralisation of ortho-phenylenediamine cpds. with hydrochloric acid and reaction with dicyandiamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2747551A1 true DE2747551A1 (en) | 1979-04-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772747551 Withdrawn DE2747551A1 (en) | 1977-10-22 | 1977-10-22 | Benzimidazolyl-guanidine cpds. prodn. - by neutralisation of ortho-phenylenediamine cpds. with hydrochloric acid and reaction with dicyandiamide |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2747551A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118344655A (en) * | 2024-06-18 | 2024-07-16 | 宿迁禾润昌新材料有限公司 | Antibacterial degradable high polymer material and preparation method thereof |
-
1977
- 1977-10-22 DE DE19772747551 patent/DE2747551A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118344655A (en) * | 2024-06-18 | 2024-07-16 | 宿迁禾润昌新材料有限公司 | Antibacterial degradable high polymer material and preparation method thereof |
| CN118344655B (en) * | 2024-06-18 | 2024-10-01 | 宿迁禾润昌新材料有限公司 | Antibacterial degradable high polymer material and preparation method thereof |
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