DE1021853B - Process for the preparation of N-substituted 2, 4-diamino-1, 3, 5-triazines - Google Patents
Process for the preparation of N-substituted 2, 4-diamino-1, 3, 5-triazinesInfo
- Publication number
- DE1021853B DE1021853B DEH27670A DEH0027670A DE1021853B DE 1021853 B DE1021853 B DE 1021853B DE H27670 A DEH27670 A DE H27670A DE H0027670 A DEH0027670 A DE H0027670A DE 1021853 B DE1021853 B DE 1021853B
- Authority
- DE
- Germany
- Prior art keywords
- salts
- diamino
- triazine
- substituted
- triazines
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Verfahren zur Herstellung von N-substituierten 2,4-Diamino-1,3,5-triazinen Die Patentanmeldung H 24 839 IVb/12p betrifft ein Verfahren zur Herstellung von N-substituierten 2,4-Diamino-1,3,5-triazinen der allgemeinen Formel worin R1 bis R4 entweder H oder ein Alkyl, ein Aryl, ein substituiertes Aryl oder einen heterocyclischen Rest bedeuten, jedoch höchstens drei der Substituenten R1 bis R4 Wasserstoff sind. Das Verfahren ist dadurch gekennzeichnet, daß die entsprechenden Biguanidhydrochloride oder andere Biguanidsalze anorganischer, flüchtiger Säuren mit Ameisensäure zu den entsprechenden Triazinderivaten umgesetzt und durch Zugabe von Säure das entsprechende Triazinsalz bzw. durch Zugabe von Lauge die Triazinbase erhalten werden.Process for the preparation of N-substituted 2,4-diamino-1,3,5-triazines The patent application H 24 839 IVb / 12p relates to a process for the preparation of N-substituted 2,4-diamino-1,3,5-triazines the general formula in which R1 to R4 are either H or an alkyl, an aryl, a substituted aryl or a heterocyclic radical, but at most three of the substituents R1 to R4 are hydrogen. The process is characterized in that the corresponding biguanide hydrochlorides or other biguanide salts of inorganic, volatile acids are reacted with formic acid to give the corresponding triazine derivatives and the corresponding triazine salt is obtained by adding acid or the triazine base is obtained by adding lye.
Es wurde nun gefunden, daß das den Biguanidsalzen entsprechende Triazinsalz ohne Säurezusatz erhältlich ist, da es sich beim Abkühlen aus dem Reaktionsgemisch abscheidet und direkt isoliert werden kann. Das isolierte Salz wird zweckmäßig mit Wasser behandelt. Geringe Mengen des Salzes hydrolysieren dabei, so daß dem Waschwasser eine kleine Säuremenge zur Verhinderung der Hydrolyse zugegeben werden muß, wenn analysenreine Produkte hergestellt werden sollen.It has now been found that the triazine salt corresponding to the biguanide salts can be obtained without the addition of acid, since it is removed from the reaction mixture on cooling deposited and can be isolated directly. The isolated salt is expedient with Treated water. Small amounts of the salt hydrolyze, so that the wash water a small amount of acid must be added to prevent hydrolysis if analytically pure products are to be produced.
Ein besonderer Vorteil des Verfahrens ist also, daß die Triazinsalze direkt anfallen. Dadurch entfällt die Überführung der Triazinbase in ihre Salze, die bei den Triazinen infolge ihrer Schwerlöslichkeit in den üblichen Lösungsmitteln außerordentlich große Lösungsmittelmengen erfordert und für die technische Gewinnung wenig geeignet ist.A particular advantage of the process is that the triazine salts incurred directly. This eliminates the need to convert the triazine base into its salts, that of the triazines due to their poor solubility in the usual solvents Requires extremely large amounts of solvent and for industrial production is not very suitable.
Des weiteren wurde gefunden, daß auch andere anorganische Säuren nichtflüchtiger Natur verwendet werden können, wobei die Ausbeute an Triazinsalz von der Löslichkeit des Biguanidsalzes in Ameisensäure abhängt.It has also been found that other inorganic acids are also more non-volatile Nature can be used, the yield of triazine salt on the solubility of the biguanide salt in formic acid.
Beispiel 1 12,5 g p-Chlorphenylbiguanidhydrochlorid werden mit 14,2 ml Ameisensäure 4 Stunden am Rückfluß gekocht und das beim Abkühlen sich abscheidende und filtrierte Reaktionsprodukt mit Wasser gewaschen.Example 1 12.5 g of p-chlorophenyl biguanide hydrochloride are added with 14.2 ml of formic acid refluxed for 4 hours and that which separates out on cooling and washed filtered reaction product with water.
Die Analyse ergab: Cl gef. 26,58 0/0, Cl ber. 27,47 0/0 für das N-p-Chlorphenyl-2,4-diamino-s-triazin-hydrochlorid, wogegen für die Base sich nur ein Cl-Wert von 16,000/0 Cl errechnet. Demnach liegen 900/, als Hydrochlorid vor. Beispiel 2 11,7 g p-Chlorphenylbiguanidsulfat wurden mit 11 ml Ameisensäure 3 Stunden gekocht. Das beim Abkühlen sich abscheidende Reaktionsprodukt vom F.210° ist das Sulfat des N-p-Chlorphenyl-2,4-diamino-s-triazins (C0 H$NäCl)2 - H2 S04 - M = 270,7.The analysis showed: Cl found. 26.58 0/0, Cl calc. 27.47 0/0 for the Np-chlorophenyl-2,4-diamino-s-triazine hydrochloride, whereas only a Cl value of 16,000 / 0 Cl is calculated for the base . According to this, 900 /, are available as hydrochloride. Example 2 11.7 g of p-chlorophenyl biguanide sulfate were boiled with 11 ml of formic acid for 3 hours. The reaction product separating out on cooling, at a temperature of 210 °, is the sulfate of Np-chlorophenyl-2,4-diamino-s-triazine (CO H $ NaCl) 2 - H2 SO4 - M = 270.7.
Berechnet ........ N = 25,890/0, Cl = 13,120/0; gefunden ......... N = 25,040/0, Cl = 12,950/0. Beispiel 3 20 g p-Toluylbiguanid-hydrochlorid wurden in 20 ml Ameisensäure 5 Stunden gekocht. Das nach Abkühlen der Lösung abgeschiedene Produkt wurde abgesaugt. F. = 2510. Calculated ........ N = 25.890 / 0, Cl = 13.120 / 0; found ......... N = 25.040 / 0, Cl = 12.950 / 0. Example 3 20 g of p-toluyl biguanide hydrochloride were boiled in 20 ml of formic acid for 5 hours. The product which separated out after the solution had cooled was filtered off with suction. F. = 2510.
Ausbeute: 710/0 N-p-Toluyl-2,4-diamino-s-triazin-hydrochlorid.Yield: 710/0 N-p-toluyl-2,4-diamino-s-triazine hydrochloride.
Beispiel 4 25 g p-Nitrophenylbiguanidhydrochlorid wurden in 90 ml Ameisensäure 5 Stunden gekocht. Das nach Abkühlen der Lösung abgeschiedene Produkt wurde abgesaugt. F. = 325°. Ausbeute: 97 °/o N-p-Nitrophenyl-2,4-diamino-s-triazinhydrochlorid.Example 4 25 g of p-nitrophenyl biguanide hydrochloride were in 90 ml Formic acid boiled for 5 hours. The product deposited after the solution has cooled was sucked off. F. = 325 °. Yield: 97% N-p-nitrophenyl-2,4-diamino-s-triazine hydrochloride.
Claims (3)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1172531D FR1172531A (en) | 1956-07-05 | 1956-07-24 | Process for the preparation of products of n-substitutions of 2, 4-diamino-1, 3, 5 triazine |
| DEH27670A DE1021853B (en) | 1956-07-26 | 1956-07-26 | Process for the preparation of N-substituted 2, 4-diamino-1, 3, 5-triazines |
| CH4796357A CH365083A (en) | 1956-07-05 | 1957-07-04 | Process for the preparation of N-substituted 2,4-diamino-1,3,5-triazines |
| FR71787D FR71787E (en) | 1956-07-05 | 1957-07-09 | Process for the preparation of n-substitution products of 2, 4-diamino-1, 3, 5 triazine |
| GB23828/57A GB867226A (en) | 1955-08-31 | 1957-07-26 | Method of producing n-substituted products of 2,4-diamino-1,3,5-triazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH27670A DE1021853B (en) | 1956-07-26 | 1956-07-26 | Process for the preparation of N-substituted 2, 4-diamino-1, 3, 5-triazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1021853B true DE1021853B (en) | 1958-01-02 |
Family
ID=7150638
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH27670A Pending DE1021853B (en) | 1955-08-31 | 1956-07-26 | Process for the preparation of N-substituted 2, 4-diamino-1, 3, 5-triazines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1021853B (en) |
-
1956
- 1956-07-26 DE DEH27670A patent/DE1021853B/en active Pending
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