DE1033210B - Process for the preparation of carbonic acid amides from imidazoles, triazoles and tetrazoles - Google Patents

Process for the preparation of carbonic acid amides from imidazoles, triazoles and tetrazoles

Info

Publication number
DE1033210B
DE1033210B DEB42718A DEB0042718A DE1033210B DE 1033210 B DE1033210 B DE 1033210B DE B42718 A DEB42718 A DE B42718A DE B0042718 A DEB0042718 A DE B0042718A DE 1033210 B DE1033210 B DE 1033210B
Authority
DE
Germany
Prior art keywords
tetrazoles
triazoles
imidazoles
carbonic acid
acid amides
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
Application number
DEB42718A
Other languages
German (de)
Inventor
Dr Heinz August Staab
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DEB42718A priority Critical patent/DE1033210B/en
Publication of DE1033210B publication Critical patent/DE1033210B/en
Pending legal-status Critical Current

Links

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
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

Verfahren zur Herstellung von Kohlensäureamiden von Imidazolen, Triazolen und Tetrazolen Es wurde gefunden, daß man Kohlensäureamide von Imidazolen, Triazolen und Tetrazolen mit einem an ein N-Atom gebundenen, reaktionsfähigen Wasserstoffatom in nahezu theoretischer Ausbeute erhält, wenn man diese stickstoffhaltigen heterocyclischen Verbindungen mit Phosgen umsetzt. Die Ausgangsverbindungen werden im allgemeinen in solchen Mengenverhältnissen miteinander umgesetzt, daß 4 Mol der heterocyclischen Verbindung auf 1 Mol Phosgen entfallen. Von den verwendeten 4 Mol der stickstoffhaltigen heterocyclischen Verbindung werden 2 Mol als entsprechendes Hydrochlorid zurückgewonnen.Process for the preparation of carbonic acid amides from imidazoles, triazoles and tetrazoles It has been found that carbonic acid amides of imidazoles, triazoles and tetrazoles having a reactive hydrogen atom bonded to an N atom Obtained in almost theoretical yield if you these nitrogen-containing heterocyclic Reacts compounds with phosgene. The starting compounds are generally reacted with one another in such proportions that 4 moles of the heterocyclic Compound for 1 mole of phosgene. Of the 4 moles used, the nitrogen-containing heterocyclic compound, 2 moles are recovered as the corresponding hydrochloride.

Zweckmäßig führt man die Reaktion in wasserfreien indifferenten organischen Lösungsmitteln durch. Besonders gut geeignet ist Tetrahydrofuran, doch lassen sich auch andere Äther, die unter den genannten Bedingungen nicht mit Phosgen reagieren, sowie aliphatische oder aromatische Kohlenwasserstoffe verwenden. Es genügt vollständig, bei Raumtemperatur zu arbeiten.The reaction is expediently carried out in anhydrous inert organic Solvents. Tetrahydrofuran is particularly suitable, but can be also other ethers that do not react with phosgene under the conditions mentioned, as well as aliphatic or aromatic hydrocarbons. It is completely sufficient to work at room temperature.

Die erhaltenen Verbindungen spalten unter hydrolysierenden Bedingungen sehr leicht Kohlendioxyd ab und lassen sich deshalb vorteilhaft als Blähmittel verwenden.The compounds obtained cleave under hydrolyzing conditions carbon dioxide very easily and can therefore be used advantageously as a blowing agent.

Die in den Beispielen genannten Teile sind Gewichtsteile.The parts mentioned in the examples are parts by weight.

Beispiel 1 In eine Lösung von 3 Teilen Imidazol in 125 Teilen wasserfreiem Tetrahydrofuran wird unter Ausschluß von Luftfeuchtigkeit Phosgen im Molverhältnis 4 : 1 eingeleitet. Ein Überschuß an Phosgen wird durch Einleiten von getrocknetem Stickstoff entfernt. Anschließend saugt man vom ausgefallenen Imidazol Hydrochlorid ab und engt die Tetrahydrofuranlösung im Vakuum ein. Umletzte Reste Imidazolhydrochlorid zu entfernen, kann man den kristallisierten Rückstand einige Male mit je 50 Teilen siedendem Benzol extrahieren. Man erhält reines N. N'-Carbonvl-di-imidazol vom Schmelzpunkt 115.5 bis 116° C.Example 1 In a solution of 3 parts of imidazole in 125 parts of anhydrous Tetrahydrofuran becomes phosgene in a molar ratio with the exclusion of atmospheric moisture 4: 1 initiated. An excess of phosgene is dried by passing in Nitrogen removed. The imidazole hydrochloride which has precipitated is then suctioned off and the tetrahydrofuran solution is concentrated in vacuo. Residual residues of imidazole hydrochloride to remove, you can the crystallized residue a few times with 50 parts Extract boiling benzene. Pure N.N'-carbonvl-di-imidazole with a melting point is obtained 115.5 to 116 ° C.

Beispiel 2 Führt man die Umsetzung, wie im Beispiel 1 beschrieben wurde, mit 2 Teilen 1,2,4-Triazol an Stelle von 3 Teilen Imidazol in 100 Teilen wasserfreiem Tetrahydrofuran. durch, so verläuft die Reaktion analog. Man erhält N,N'-Carbonyl-di-triazol vom Schmelzpunkt 136° C in theoretischer Ausbeute.Example 2 If the reaction is carried out as described in Example 1 was, with 2 parts 1,2,4-triazole instead of 3 parts imidazole in 100 parts anhydrous tetrahydrofuran. through, the reaction proceeds analogously. You get N, N'-carbonyl-di-triazole with a melting point of 136 ° C. in theoretical yield.

Beispiel 3 In eine Lösung von 4,7 Teilen Benzimidazol in 125 Teilen wasserfreiem Tetrahydrofuran wird unter Ausschluß von Luftfeuchtigkeit ein Teil gasförmiges Phosgen im Lauf von 5 Minuten eingeleitet. Man saugt von dem ausgefallenen Benzimidazolhydrochlorid ab. Das Filtrat hinterläßt beim Einengen im Vakuum bei etwa 40°C weiße Kristalle von N,N'-Carbonyl-di-benzimidazol. Beim Umkristallisieren aus wasserfreiem Benzol erhält man farblose Nadeln vom Schmelzpunkt 182 bis 183° C.Example 3 Into a solution of 4.7 parts of benzimidazole in 125 parts anhydrous tetrahydrofuran becomes part with the exclusion of atmospheric moisture initiated gaseous phosgene in the course of 5 minutes. One sucks off the fancy Benzimidazole Hydrochloride. The filtrate leaves on concentration in vacuo about 40 ° C white crystals of N, N'-carbonyl-di-benzimidazole. When recrystallizing colorless needles with a melting point of 182 ° to 183 ° are obtained from anhydrous benzene C.

Beispiel 4 Wie im Beispie13 beschrieben wurde, setzt man 4,75 Teile Benztriazol mit 1 Teil Phoegen um und arbeitet das Reaktionsgernisch in gleicher Weise auf. Beim Umkristallisieren aus wasserfreiem Benzol erhält man das N,N'-Carbonyl-di-benztriazol vom Schmelzpunkt 183 bis 185°C (und Zersetzung) in farblosen Nadeln.Example 4 As described in Example 13, 4.75 parts are used Benztriazole with 1 part of Phoegen and the reaction mixture works in the same way Way up. Recrystallization from anhydrous benzene gives the N, N'-carbonyl-di-benzotriazole from melting point 183 to 185 ° C (and decomposition) in colorless needles.

Claims (1)

PATENTANSPRUCH- Verfahren zur Herstellung von Kohlensäureamiden von Imidazolen, Triazolen und Tetrazolen mit einem an ein Stickstoffatom gebundenen, reaktionsfähigen Wasserstoffatom, dadurch gekennzeichnet, daß diese Verbindungen mit Phosgen umgesetzt werden. PATENT CLAIM- Process for the preparation of carbonic acid amides of imidazoles, triazoles and tetrazoles with a reactive hydrogen atom bonded to a nitrogen atom, characterized in that these compounds are reacted with phosgene.
DEB42718A 1956-12-06 1956-12-06 Process for the preparation of carbonic acid amides from imidazoles, triazoles and tetrazoles Pending DE1033210B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB42718A DE1033210B (en) 1956-12-06 1956-12-06 Process for the preparation of carbonic acid amides from imidazoles, triazoles and tetrazoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB42718A DE1033210B (en) 1956-12-06 1956-12-06 Process for the preparation of carbonic acid amides from imidazoles, triazoles and tetrazoles

Publications (1)

Publication Number Publication Date
DE1033210B true DE1033210B (en) 1958-07-03

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3374241A (en) * 1962-07-23 1968-03-19 Du Pont Diphenylcarbamyl derivatives of certain azoles
EP0692476A2 (en) 1994-07-11 1996-01-17 Bayer Ag Improved process for the preparation of N,N'-carbonyldiazoles, specifically N,N-carbonyl-diimidazole
US6392057B1 (en) 1998-07-28 2002-05-21 Bayer Aktiengesellschaft Method for the production of n,n′-carbonyldiazoles
JP2002265454A (en) * 2001-03-09 2002-09-18 Hodogaya Chem Co Ltd Benzimidazole derivative and curable composition
US6465658B2 (en) 2000-07-19 2002-10-15 Bayer Aktiengesellschaft Process for the preparation of N,N′-carbonyldiazoles and azolide salts
WO2005063718A1 (en) 2003-12-19 2005-07-14 Saltigo Gmbh Method for the production of n,n -carbonyldiazoles
US7102012B2 (en) 2004-05-13 2006-09-05 Lanxess Deutschland Gmbh Process for preparing N,N'-carbonyldiazoles

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3374241A (en) * 1962-07-23 1968-03-19 Du Pont Diphenylcarbamyl derivatives of certain azoles
EP0692476A2 (en) 1994-07-11 1996-01-17 Bayer Ag Improved process for the preparation of N,N'-carbonyldiazoles, specifically N,N-carbonyl-diimidazole
EP0692476A3 (en) * 1994-07-11 1997-09-03 Bayer Ag Improved process for the preparation of N,N'-carbonyldiazoles, specifically N,N-carbonyl-diimidazole
US6392057B1 (en) 1998-07-28 2002-05-21 Bayer Aktiengesellschaft Method for the production of n,n′-carbonyldiazoles
US6774239B2 (en) 2000-07-19 2004-08-10 Bayer Aktiengesellschaft Process for the preparation of N,N′-carbonyldiazoles and azolide salts
US6465658B2 (en) 2000-07-19 2002-10-15 Bayer Aktiengesellschaft Process for the preparation of N,N′-carbonyldiazoles and azolide salts
JP2002265454A (en) * 2001-03-09 2002-09-18 Hodogaya Chem Co Ltd Benzimidazole derivative and curable composition
WO2005063718A1 (en) 2003-12-19 2005-07-14 Saltigo Gmbh Method for the production of n,n -carbonyldiazoles
JP2007514670A (en) * 2003-12-19 2007-06-07 サルティゴ・ゲーエムベーハー Process for producing N, N-carbonyldiazoles
US7888515B2 (en) 2003-12-19 2011-02-15 Saltigo Gmbh Method for the production of N,N-carbonyldiazoles
JP4795968B2 (en) * 2003-12-19 2011-10-19 サルティゴ・ゲーエムベーハー Process for producing N, N-carbonyldiazoles
KR101148247B1 (en) * 2003-12-19 2012-05-21 잘티고 게엠베하 Method for the Production of N,N'-carbonyldiazoles
US7102012B2 (en) 2004-05-13 2006-09-05 Lanxess Deutschland Gmbh Process for preparing N,N'-carbonyldiazoles

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