DE1668101A1 - Process for the preparation of hydrogen-substituted phosphate heterocycles - Google Patents
Process for the preparation of hydrogen-substituted phosphate heterocyclesInfo
- Publication number
- DE1668101A1 DE1668101A1 DE19681668101 DE1668101A DE1668101A1 DE 1668101 A1 DE1668101 A1 DE 1668101A1 DE 19681668101 DE19681668101 DE 19681668101 DE 1668101 A DE1668101 A DE 1668101A DE 1668101 A1 DE1668101 A1 DE 1668101A1
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- general formula
- group
- heterocycles
- compound
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 229910019142 PO4 Inorganic materials 0.000 title 1
- 239000010452 phosphate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 13
- -1 Is aroxy Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HPUPGAFDTWIMBR-UHFFFAOYSA-N [methyl(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(C)OC1=CC=CC=C1 HPUPGAFDTWIMBR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- KLFXGMZYFVBYAR-UHFFFAOYSA-N methyl(phenoxy)phosphinic acid Chemical compound CP(O)(=O)OC1=CC=CC=C1 KLFXGMZYFVBYAR-UHFFFAOYSA-N 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Verfahren zur Herstellung von waseerstoffaubstituierten Phosphazenheterocyclen Verbindungen mit einer wasserstoffsubstituierten Phosphazengruppierung H-P=N-sind bislang unbekannt, inabesondere kennt man auch keine Heterocyclen, die diese Gruppierung als Ringglied enthalten. Process for the preparation of hydrogen-substituted phosphazene heterocycles Compounds with a hydrogen-substituted phosphazene group are H-P = N- hitherto unknown, in particular no heterocycles containing this group are known included as a ring link.
Es wurde nun gefunden, daB solche am Phosphor wasserstofftragende Phosphazenheterocyclen entstehen, wenn man eine Verbindung der allgemeinen Formel H2N-Bn-A I worin n 1 oder 2 ist, B fUr die Gruppe Z=Y und A fUr die Gruppe IXH oder =X-NH- (X ist B zugewandt) steht, worin X, Y und Z gegebenenfalls substituierte Kohlenstoff-oder Ehoaphorglieder bezelchnen und Y oder Z auch Stickstoff aein kann, wobei im Falle Z und X gleich Phosphor, Y gleich Stickstoff oder Kohlenstoff ist, im Falle n = 2 in den beiden Gruppen B die Glieder Y und Z in ihrer Bedeutung nicht übereinzustimmen brauchen, die Glieder Z und Y auch Bestandteil eines carbocyclischen oder heterocyclischen 5-bis 12-Ringes sein können (vorzugsweise 5-bis 7-Ring), und die Gruppe =X-NH-auch einen gegebenenfalls anellierten heterocyclischen 5-bis 12- (vorzugsweise 5-bis 7-)-Ring bilden kann, mit mindestens der stochiometrischen Menge einer Verbindung der allgemeinen Formel II R2-P (OR3) 2 II worin R2 ein gegebenenfalls substituierter Alkyl-, Aryl-, Aroxy-, Aralkyl-oder Alkoxyrest ist, weiterhin R3 einen gegebenenfalls substituierten Arylrest bedeutet, gegebenenfalls unter vermindertem Druck im Temperaturbereich von etwa 20° bis etwa 300° C umsetzt.It has now been found that those on phosphorus carry hydrogen Phosphazene heterocycles are formed when a compound of the general formula H2N-Bn-A I where n is 1 or 2, B for the group Z = Y and A for the group IXH or = X-NH- (X faces B), in which X, Y and Z are optionally substituted Denote carbon or ehoaphor members and Y or Z can also be nitrogen, whereby in the case of Z and X is phosphorus, Y is nitrogen or carbon, in the case n = 2 in the two groups B the terms Y and Z do not match in their meaning need the members Z and Y also part of a carbocyclic or heterocyclic Can be 5- to 12-ring (preferably 5- to 7-ring), and the group = X-NH- also an optionally fused heterocyclic 5- to 12- (preferably 5-bis 7 -) - ring can form, with at least the stoichiometric amount of a compound of the general formula II R2-P (OR3) 2 II wherein R2 is an optionally substituted one Is alkyl, aryl, aroxy, aralkyl or alkoxy, and R3 is optionally substituted aryl radical, optionally under reduced pressure in the temperature range from about 20 ° to about 300 ° C.
Ale Substituenten für die Glieder X, Y und Z der Komponente I seien genannt : Wasserstoff (im Falle von Kohlenstoff), gegebenenfalls bis zu zwei Doppelbindungen enthaltendee Alkyl mit 1-10 (vorzugsweise 1-6) Kohlenstoffatonen, gegebenenfalls durch Halogen (vorzugsweise Fluor, Chlor, Brom), Nitro, CN, niederes Dialkylamino, niederes Alkyl, niederes Alkoxy, SO3R (R gleich Alkyl mit 1-6 C-Atomen), Phenyl, substituierter Arylrest mit 1-10 Kohlenstoffatomen (vorzugsweise Phenyl) ; ferner Aminogruppen, die ein-oder zweifach durch vorstehend genannte Substituenten substituiert sein können.All substituents for members X, Y and Z of component I are called: hydrogen (in the case of carbon), optionally up to two double bonds containing alkyl of 1-10 (preferably 1-6) carbon atoms, optionally by halogen (preferably fluorine, chlorine, bromine), nitro, CN, lower dialkylamino, lower alkyl, lower alkoxy, SO3R (R equals alkyl with 1-6 carbon atoms), phenyl, substituted Aryl radical with 1-10 carbon atoms (preferably Phenyl); furthermore amino groups which are substituted once or twice by the abovementioned substituents can be substituted.
Als für das erfindungsgemäBe Verfahren Verwendung findende Verbindungen der allgemeinen Formel I seien unter anderem folgende beispielhaft genannt : R = CH3, C6H5 R = H, CH3, C2H5, Allyl R = H, R' = iC3H7 R = C2H5, R' = pClC6H4 R = H, R' = pCH3OC6H4 R = R'= CH3 R = R'= Allyl R = C2H5, R' = pCH3C6H4 R = H, R' = pClC6H4 R = iC3H7, R' = pclC6H4, pNO2C6H4, pCNO6H4, pC6H5C6H4 Die Ausgangsverbindungen sind bekannt bzw. können nach bekannten Verfahren erhalten werden. Gegebenenfalls kann es zweckmäßig sein, sie erst vor der eigentlichen Umsetzung aus dem entsprechenden Chlorid oder einem anderen Salz mit der erforderlichen Menge Alkalialkoholat bzw. Alkaliamid in Freiheit zu setzen, und gegebenenfalls den mitverwendeten Alkohol zu entfernen.Examples of compounds of the general formula I which can be used for the process according to the invention include the following: R = CH3, C6H5 R = H, CH3, C2H5, allyl R = H, R '= iC3H7 R = C2H5, R' = pClC6H4 R = H, R '= pCH3OC6H4 R = R' = CH3 R = R '= allyl R = C2H5, R '= pCH3C6H4 R = H, R' = pClC6H4 R = iC3H7, R '= pclC6H4, pNO2C6H4, pCNO6H4, pC6H5C6H4 The starting compounds are known or can be obtained by known processes. It may be appropriate to set them free from the corresponding chloride or another salt with the required amount of alkali metal alcoholate or alkali amide before the actual reaction and, if necessary, to remove the alcohol used.
Erfindungsgemäß verwendete Verbindungen der Formel II sind solche, in denen R2 ein gegebenenfalls durch NO2, CN, Halogen (vorzugsweise Fluor, Chlor, Brom) substituierter, gegebenenfalls bis zu zwei Doppelbindungen oder eine Dreifachbindung enthaltender Alkyl-oder Alkoxyrest mit 1 bis 12 Kohlenstoffatomen, vorzugeweise 1 bis 6, ganz besonders bevorzugt mit 1 bis 4 Kohlenstoffatomen ist, weiterhin ein gegebenenfalls durch vorstehend genannte Substituenten substituierter Cycloalkyl-oder Cycloalkoxyrest mit 4 bis 10 Ringgliedern (vorzugsweise 5 oder 6) ist; ferner R2 auch ein gegebenenfalls durch Nitro, CN, niederes Alkyl, niederes Alkoxy, Halogen (vorzugsweise Fluor, Chlor, Brom) substituierter Arylrest mit bis zu 10 Kohlenstoffatomen (vorzugsweise Phenyl), Aralkyl-oder Aralkoxyrest mit insgesamt bis zu 12 Kohlenstoffatomen (vorzugsweise Aryl = Phenyl, Alkyl mit 1-4 C-Atomen) oder gleich OR3 ist. R3 ist ein gegebenenfalls durch Nitro, CN, niederes Alkyl-oder Alkoxy, Halogen substituierter Arylrest, vorzugsweise Phenyl.Compounds of the formula II used according to the invention are those in which R2 is optionally replaced by NO2, CN, halogen (preferably fluorine, chlorine, Bromine) substituted, optionally up to two double bonds or a triple bond containing alkyl or alkoxy radical with 1 to 12 carbon atoms, is preferably 1 to 6, very particularly preferably 1 to 4 carbon atoms, furthermore one which is optionally substituted by the abovementioned substituents Cycloalkyl or cycloalkoxy radical with 4 to 10 ring members (preferably 5 or 6) is; furthermore R2 is also an optionally substituted by nitro, CN, lower alkyl, lower Alkoxy, halogen (preferably fluorine, chlorine, bromine) substituted aryl radical with up to to 10 carbon atoms (preferably phenyl), aralkyl or aralkoxy radical with a total of up to 12 carbon atoms (preferably aryl = phenyl, alkyl with 1-4 carbon atoms) or is equal to OR3. R3 is an optionally substituted by nitro, CN, lower alkyl or Alkoxy, halogen-substituted aryl radical, preferably phenyl.
Beispielhaft seien folgende Verbindungen genannt : P (OC6H5) 3, CH3P (OC6H5)2, C2H5P(OC6H5)2, C2H50P (OC6H5) 2' C6H11OP(OC6H5)2, Das erfindungsgem§Be Verfahren kann durch folgende Gleichung beispielhaft erlEutert werden : Durch Verwendung von Komponenten I, in der n den Wert 2 hat, sind nach dem erfindungsgemäßen Verfahren auch die entsprechenden Heterocyclen mit 8 Ringgliedern zuganglich.The following compounds may be mentioned as examples: P (OC6H5) 3, CH3P (OC6H5) 2, C2H5P (OC6H5) 2, C2H50P (OC6H5) 2 'C6H11OP (OC6H5) 2, The method according to the invention can be exemplified by the following equation: By using component I in which n has the value 2, the corresponding heterocycles with 8 ring members are also accessible by the process according to the invention.
Erfindungsgemäß werden äquimolare Mengen der Komponenten ohne weiteren Zusatz bis im Temperaturbereich von etwa 20° bis etwas 300 C, vorzugsweise zwischen etwa 40° und etwa 200° C, ganz besonders bevorzugt zwischen etwa 40° und etwa 100° C, bis zur beginnenden Phenolabspaltung erhitzt.According to the invention, equimolar amounts of the components are readily available Addition up to in the temperature range from about 20 ° to about 300 ° C., preferably between about 40 ° and about 200 ° C, very particularly preferably between about 40 ° and about 100 ° C, heated until phenol begins to split off.
ZweckmäBig nimmt man die Umsetzung im Vakuum vor, wobei das Phenol abdestilliert. Zur Vervollständigung der Reaktion wird die Temperatur langsam um 50° bis 100° C gesteigert. Im Reaktionsgefäß bleibt das rohe Produkt zurück und kann daraus anschließend destilliert, sublimiert oder umkrietallisiert weiden.The reaction is expediently carried out in vacuo, with the phenol distilled off. To complete the reaction, the temperature is slowly increased 50 ° to 100 ° C increased. The crude product remains in the reaction vessel and can then be distilled, sublimed or recrystallized from it.
Die nach dem erfindungsgemäßen Verfahren erhältlichen Verbindungen sind neu und entsprechen der allgemeinen Formel worin A, B, n und R2 die vorstehend genannte Bedeutung haben, wobei Heterocyclen mit n = 1 bevorzugt sind.The compounds obtainable by the process according to the invention are new and correspond to the general formula in which A, B, n and R2 have the abovementioned meanings, heterocycles with n = 1 being preferred.
Beispiele dafür sind: Die neuen Verbindungen können als Kunststoffhilfsprodukte sowie als Schmiermittelzusätze Verwendung finden.Examples are: The new compounds can be used as plastic auxiliaries and as lubricant additives.
Beispiel 1 : 1,1,3,3-Tetraphenyl-phenoxy-cyclotriphosphazen Das Gemisch äquimolarer Mengen von Tetraphenyl-aminodiphosphazen und Triphenylphosphit wird in einem auf 0, 2 Torr evakuierten Gefäß auf 100° und langsam ansteigend auf 200° C erhitzt. Pehnol destilliert in die Vorlage. Der Riickstand wird aus Benzol umkristallisiert. Ausbeute an analysenreiner Verbindung : 67 % der Theorie, Schmelzpunkt 153° C.Example 1: 1,1,3,3-Tetraphenyl-phenoxy-cyclotriphosphazene The mixture equimolar amounts of tetraphenyl-aminodiphosphazene and triphenylphosphite is in a vessel evacuated to 0.2 Torr to 100 ° and slowly increasing to 200 ° C heated. Pehnol distilled into the template. The residue is recrystallized from benzene. Yield of analytically pure compound: 67% of theory, melting point 153 ° C.
Ber. : C 67, 04 H 4,88 N 7,82 % Gef. : C 67, 50 H 4, 90 N 7,71% Mol.-Gewicht : Gef. : 537 (Benzol) Ber. : 537, 5 Beispiel 2 : 1, 1, 3, 3-Tetraphenyl-methyl-cyclotriphosphazen Das Gemisch äquimolarer Mengen von Tetraphenyl-aminodiphosphazen und Methylphosphonsäure-diphenylester werden wie vorstehend auf 50 bis 100° C erhitzt und das Produkt aufgearbeitet. Ber. : C 67.04 H 4.88 N 7.82% Found: C 67.50 H 4, 90 N 7.71% mole weight : Found: 537 (benzene) calc. : 537, 5 Example 2: 1, 1, 3, 3-tetraphenyl-methyl-cyclotriphosphazene The mixture of equimolar amounts of tetraphenyl-aminodiphosphazene and diphenyl methylphosphonate are heated to 50 to 100 ° C as above and the product is worked up.
Ausbeute : 69','o der Theorie an analysenreiner Verbindung, Schmelzpunkt 152° C.Yield: 69% of the theory of analytically pure compound, melting point 152 ° C.
Ber. : C 65, 36 H 5,27 N 9,15 % Gef. : C 65,62H5,46N9,07 Mol-Gewicht : Gef. : 458 (CHCl3) Ber. : 459, 4 Beispiel 3 : 2-Methyl-4-amino-6-dimethylamino-phospha-1, 3, 5-triazin Gleiche Molmengen N, N-Dimethylbiguanid und Methylphosphonsäuredephenylester werden bei 0, 05 Torr auf 40° bis 80° C erhitzt. Nach einem Vorlauf Phenol geht das Produkt bei ca. Ber. : C 65.36 H 5.27 N 9.15% Found: C 65.62H5.46 N 9.07 mole weight : Found: 458 (CHCl3) calc. : 459, 4 Example 3: 2-methyl-4-amino-6-dimethylamino-phospha-1, 3, 5-triazine Equal molar amounts of N, N-dimethylbiguanide and phenyl methylphosphonate are heated to 40 ° to 80 ° C at 0.05 Torr. After a forerun there is phenol the product at approx.
150° C und 0, 1 Torr tuber und erstarrt in der Volage. 150 ° C and 0.1 Torr tuber and solidifies in the volage.
31P-NMR (CH2Cl): Doppelquartett =-29.0 ppm, JHP = 510 Hz, JHCP 13p8 Hz. 31P-NMR (CH2Cl): double quartet = -29.0 ppm, JHP = 510 Hz, JHCP 13p8 Hz.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0054904 | 1968-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1668101A1 true DE1668101A1 (en) | 1971-06-03 |
Family
ID=7107414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681668101 Pending DE1668101A1 (en) | 1968-02-24 | 1968-02-24 | Process for the preparation of hydrogen-substituted phosphate heterocycles |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1668101A1 (en) |
-
1968
- 1968-02-24 DE DE19681668101 patent/DE1668101A1/en active Pending
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