CH405332A - Process for making new benzotriazinones - Google Patents
Process for making new benzotriazinonesInfo
- Publication number
- CH405332A CH405332A CH1042661A CH1042661A CH405332A CH 405332 A CH405332 A CH 405332A CH 1042661 A CH1042661 A CH 1042661A CH 1042661 A CH1042661 A CH 1042661A CH 405332 A CH405332 A CH 405332A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- carbon atoms
- radical
- benzotriazinones
- branched alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- DMSSTTLDFWKBSX-UHFFFAOYSA-N 1h-1,2,3-benzotriazin-4-one Chemical class C1=CC=C2C(=O)N=NNC2=C1 DMSSTTLDFWKBSX-UHFFFAOYSA-N 0.000 title claims description 5
- -1 alkyl radicals Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- INSSYZYYMPOCNO-UHFFFAOYSA-N 2,3-dihydro-1h-1,2,3-benzotriazin-4-one Chemical class C1=CC=C2C(=O)NNNC2=C1 INSSYZYYMPOCNO-UHFFFAOYSA-N 0.000 claims description 3
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical compound N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung neuer Benzotriazinone
Es wurde gefunden, dass man zu einer Gruppe neuer, diuretisch ausserordentlich wirksamer Benzotriazinone der Formeln
EMI1.1
gelangt, in welchen R gleiche oder verschiedene Bedeutung haben und Wasserstoff oder gegebenenfalls verzweigte Alkylreste mit 1 bis 6 C-Atomen, Aralkyloder Arylreste sind und R' Wasserstoff oder einen, vorzugsweise in 7-Stellung befindlichen, gegebenenfalls verzweigten Alkylrest mit 1 bis 6 C-Atomen, einen Alkoxyrest oder Halogen und R" Wasserstoff oder einen gegebenenfalls verzweigten Alkylrest mit 1 bis 6 C-Atomen bedeutet, wenn man Anthranilsäureamide der Formel
EMI1.2
in welcher R, R' und R" die oben angegebene Bedeutung haben, jedoch mit der Massgabe, dass mindestens eines der beiden R" Wasserstoff ist, mit salpetriger Säure zur Umsetzung bringt,
wobei man gegebenenfalls in der Sulfonamidogruppe vorhandene Wasserstoffatome nachträglich noch gegen den Alkyl-, Aralkyl- oder Arylrest austauschen kann.
Die nach dem vorstehend beschriebenen Verfahren erhältlichen Verbindungen lassen sich auch als Zwischenprodukte für die Herstellung der entsprechenden 1,2,3,4-Tetrahydro-benzotriazinone verwenden, indem man das betreffende 4-Oxo-6-sulfonamido-benzo-1,2, 3-triazin einer Hydrierung, vorzugsweise mittels katalytisch erregten Wasserstoffes, unterwirft.
Beispiel
15 g 2-Amino-4-chlor-5-sulfonamido-benzosäureamid werden unter Zugabe von 153 ml Wasser, 11 ml Eisessig und 1,52 ml 38%iger HCI unter kräftigem Rühren suspendiert. Zu dieser Suspension gibt man unter Eiskühlung 30 ml einer Lösung, die 6,1 g Natriumnitrit enthält, wobei man Vorsorge trifft, dass die Temperatur während der Zugabe nicht über 100 ansteigt. Nach Beendigung der Reaktion wird der Hauptanteil der Lösungsmittel im Vakuum (12 mm Hg) abgedampft, worauf Abkühlen des 7-Chlor-4-oxo 6-sulfonamido-3, 4-dihydro-(benzo-1, 2, 3-triazin) bzw. 7 Chlor - 4. hydroxy-6-sulfonamido - (benzo-1,2,3-triazin) auskristallisiert.
Analyse: ber.: Cd 13,66 N 21,50 S 12,30 gef.: Cm 13,63 N 21,42 S 12,22 Das IR-Spektrum (Nujol) zeigt folgende Hauptabsorp tionsmaxima: 5,8 : 5,9 y; ; 6,21 ; 7,39 X.
Zur Überführung in das entsprechende 1,2,3,4-Te- trahydro-benzotriazinon kann man 5,2 g dieser Verbindung in 200 ml 95% dem Alkohol suspendieren und in Gegenwart von 2 g Raney-Nickel bei 600 hydrieren, bis die theoretische H2-Menge (0,506 Ltr.) aufgenommen worden ist. Durch Zugabe von 50%igem Alkohol und Erhitzen wird das hydrierte Produkt in Lösung gebracht, worauf man diese vom Katalysator trennt und im Vakuum eindampft. Der Rückstand wird aus 125 ml 50% igem Alkohol unter Beigabe von Aktivkohle umkristallisiert. Ausbeute: 2,5 g 7-Chlor-4-oxo-6 sulfonamido-1, 2, 3, -tetrahydro-(benzo-1, 2, 3-triazin) vom Smp. 229-230 .
Process for making new benzotriazinones
It has been found that a group of new, diuretically extraordinarily effective benzotriazinones of the formulas
EMI1.1
arrives, in which R have the same or different meanings and hydrogen or optionally branched alkyl radicals with 1 to 6 carbon atoms, aralkyl or aryl radicals and R 'are hydrogen or an optionally branched alkyl radical with 1 to 6 C- preferably in the 7-position Atoms, an alkoxy radical or halogen and R "denotes hydrogen or an optionally branched alkyl radical having 1 to 6 carbon atoms when using anthranilic acid amides of the formula
EMI1.2
in which R, R 'and R "have the meaning given above, but with the proviso that at least one of the two R" is hydrogen, reacts with nitrous acid,
it being possible for any hydrogen atoms present in the sulfonamido group to be subsequently exchanged for the alkyl, aralkyl or aryl radical.
The compounds obtainable by the process described above can also be used as intermediates for the preparation of the corresponding 1,2,3,4-tetrahydrobenzotriazinones by using the 4-oxo-6-sulfonamido-benzo-1,2,3 -triazine to a hydrogenation, preferably by means of catalytically excited hydrogen, subjected.
example
15 g of 2-amino-4-chloro-5-sulfonamido-benzoic acid amide are suspended with the addition of 153 ml of water, 11 ml of glacial acetic acid and 1.52 ml of 38% HCl with vigorous stirring. 30 ml of a solution containing 6.1 g of sodium nitrite are added to this suspension while cooling with ice, taking care that the temperature does not rise above 100 during the addition. After the reaction has ended, most of the solvent is evaporated off in vacuo (12 mm Hg), whereupon the 7-chloro-4-oxo 6-sulfonamido-3, 4-dihydro- (benzo-1, 2, 3-triazine) or 7 Chlorine - 4. hydroxy-6-sulfonamido - (benzo-1,2,3-triazine) crystallized out.
Analysis: calculated: Cd 13.66 N 21.50 S 12.30 found: Cm 13.63 N 21.42 S 12.22 The IR spectrum (Nujol) shows the following main absorption maxima: 5.8: 5, 9 y; ; 6.21; 7.39 X.
To convert to the corresponding 1,2,3,4-tetrahydrobenzotriazinone, 5.2 g of this compound can be suspended in 200 ml of 95% alcohol and hydrogenated in the presence of 2 g of Raney nickel at 600 until the theoretical H2 amount (0.506 liters) has been absorbed. The hydrogenated product is brought into solution by adding 50% strength alcohol and heating, whereupon this is separated from the catalyst and evaporated in vacuo. The residue is recrystallized from 125 ml of 50% alcohol with the addition of activated charcoal. Yield: 2.5 g of 7-chloro-4-oxo-6 sulfonamido-1, 2, 3, -tetrahydro- (benzo-1, 2, 3-triazine) of melting point 229-230.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1042661A CH405332A (en) | 1962-02-05 | 1962-02-05 | Process for making new benzotriazinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1042661A CH405332A (en) | 1962-02-05 | 1962-02-05 | Process for making new benzotriazinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH405332A true CH405332A (en) | 1966-01-15 |
Family
ID=4363103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1042661A CH405332A (en) | 1962-02-05 | 1962-02-05 | Process for making new benzotriazinones |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH405332A (en) |
-
1962
- 1962-02-05 CH CH1042661A patent/CH405332A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH405332A (en) | Process for making new benzotriazinones | |
| DE1301312B (en) | Process for the preparation of pyrryl (2) acetonitriles | |
| DE69132772T2 (en) | Manufacture of boric acid derivatives | |
| US3152168A (en) | Haloalkyl pentahalophenyl carbonates | |
| DE833818C (en) | Process for the preparation of new mono- and diquartar salts of pyrimidylaminocinnolines | |
| DE945509C (en) | Process for the preparation of thiobarbituric acid derivatives | |
| DE942149C (en) | Process for the preparation of substituted glycine amides | |
| CH630616A5 (en) | METHOD FOR PRODUCING 5-NITROSO-2,4,6-TRIAMINOPYRIMIDINE. | |
| DE1806867B2 (en) | Process for the preparation of substituted 4-hydroxypyrimidines | |
| AT222816B (en) | Process for the preparation of 2-cis-β-ionylideneacetic acid | |
| DE3808355A1 (en) | 1-Naphthoic acid and its functional compounds, their preparation, and their use in crop protection | |
| DE822552C (en) | Process for the preparation of alkyl derivatives of diketooxazolidines | |
| DE936686C (en) | Process for the preparation of 2-amino-5- (2'-oxyaethyl) -oxazole- (1, 3) | |
| AT200137B (en) | Process for the preparation of new tertiary amines of the tetrahydrofuran series | |
| AT229873B (en) | Process for the preparation of 1,4-disubstituted piperazine derivatives | |
| DE614461C (en) | Process for the production of isochromanes | |
| DE2166115A1 (en) | 2,6 Methano 3 benzazocine excreted from 2127819 | |
| AT200136B (en) | Process for the preparation of new tertiary amines of the tetrahydrofuran series | |
| DE1113696B (en) | Process for the preparation of 1,3-disubstituted or 1,3,8-trisubstituted 9-methylisoxanthines | |
| AT367411B (en) | METHOD FOR PRODUCING NEW 4-AMINO-1,2 CARBON SUBSTITUTED PYRAZOLIDINES AND THEIR SALTS | |
| DE965404C (en) | Process for the preparation of 2-methylcyclopentanedione- (1,3) | |
| DE940831C (en) | Process for the preparation of a pyridopyrimidinedione | |
| AT211819B (en) | Process for the preparation of new aryloxyacetic acid amides | |
| DE854521C (en) | Process for the preparation of phenanthridine compounds | |
| AT239799B (en) | Process for the preparation of new aryl-N-substituted thionocarbamates |