PL416560A1 - Sposób otrzymywania czwartorzędowych soli N-(4,6-dipodstawionych-1,3,5-triazyn-2-ylo)-amoniowych kwasów sulfonowych - Google Patents
Sposób otrzymywania czwartorzędowych soli N-(4,6-dipodstawionych-1,3,5-triazyn-2-ylo)-amoniowych kwasów sulfonowychInfo
- Publication number
- PL416560A1 PL416560A1 PL416560A PL41656016A PL416560A1 PL 416560 A1 PL416560 A1 PL 416560A1 PL 416560 A PL416560 A PL 416560A PL 41656016 A PL41656016 A PL 41656016A PL 416560 A1 PL416560 A1 PL 416560A1
- Authority
- PL
- Poland
- Prior art keywords
- organic solvent
- solution
- substituted
- disubstituted
- alkyl
- Prior art date
Links
- -1 N-(4,6-disubstituted-1,3,5-triazin-2-yl)-ammonium sulfonic acids Chemical class 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 5
- 150000003839 salts Chemical group 0.000 title abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 abstract 3
- 238000005956 quaternization reaction Methods 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 abstract 2
- 125000002619 bicyclic group Chemical class 0.000 abstract 2
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 abstract 2
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 abstract 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 abstract 2
- 150000003512 tertiary amines Chemical class 0.000 abstract 2
- 235000001258 Cinchona calisaya Nutrition 0.000 abstract 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 abstract 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229960001404 quinidine Drugs 0.000 abstract 1
- 229960000948 quinine Drugs 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Przedmiotem zgłoszenia jest sposób otrzymywania czwartorzędowych soli N-(4,6-dipodstawionych-1,3,5-triazyn-2-ylo)-amoniowych kwasów sulfonowych, o wzorze ogólnym 1, w którym R1, R2 oznaczają grupy alkilowe lub benzylowe, R3, R4, R5 oznaczają podstawniki alkilowe lub podstawione alkilowe aminy trzeciorzędowej lub tworzą N-podstawiony układ cykliczny lub bicykliczny zwłaszcza z atomem azotu w położeniu przyczółkowym, w którym R3, R4, R5 tworzą N-podstawiony układ bicykliczny wywodzący się ze strychniny, brucyny, chininy, chinidyny, cynchoniny lub cynchonidyny, natomiast -O-SO2R6 oznacza anion kwasu sulfonowego, w którym R6 oznacza grupę alkilową, podstawioną grupę alkilową, cykloalkilową, podstawioną grupę cykloalkilową, arylową, podstawioną grupę arylową, polega na tym, że z roztworu kwasu sulfonowego o wzorze R6SO2-OH, w którym R6 ma wyżej podane znaczenie, w rozpuszczalniku organicznym i z roztworu aminy trzeciorzędowej o wzorze NR3R4R5, w którym R3, R4, R5 mają wyżej podane znaczenie, w rozpuszczalniku organicznym sporządza się mieszaninę, do której wprowadza się w dowolnej kolejności akceptor chlorowodoru użyty w nadmiarze oraz roztwór 2-chloro-4,6-dipodstawionej-1,3,5-triazyny w rozpuszczalniku organicznym i prowadzi proces czwartorzędowania, a po zakończeniu reakcji czwartorzędowania wydziela się produkt finalny. Sposób polega także na tym, że sporządza się zawiesinę akceptora chlorowodoru w rozpuszczalniku organicznym, do której wprowadza się mieszaninę roztworu kwasu sulfonowego i roztworu aminy trzeciorzędowej, a następnie dodaje się roztwór 2-chloro-4,6-dipodstawionej-1,3,5-triazyny w rozpuszczalniku organicznym i prowadzi proces czwartorzędowania.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL416560A PL241161B1 (pl) | 2016-03-21 | 2016-03-21 | Sposób otrzymywania czwartorzędowych soli N-(4,6-dipodstawionych-1,3,5-triazyn-2-ylo)-amoniowych kwasów sulfonowych |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL416560A PL241161B1 (pl) | 2016-03-21 | 2016-03-21 | Sposób otrzymywania czwartorzędowych soli N-(4,6-dipodstawionych-1,3,5-triazyn-2-ylo)-amoniowych kwasów sulfonowych |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL416560A1 true PL416560A1 (pl) | 2017-09-25 |
| PL241161B1 PL241161B1 (pl) | 2022-08-16 |
Family
ID=59897553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL416560A PL241161B1 (pl) | 2016-03-21 | 2016-03-21 | Sposób otrzymywania czwartorzędowych soli N-(4,6-dipodstawionych-1,3,5-triazyn-2-ylo)-amoniowych kwasów sulfonowych |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL241161B1 (pl) |
-
2016
- 2016-03-21 PL PL416560A patent/PL241161B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL241161B1 (pl) | 2022-08-16 |
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