PL438656A1 - Ligand salphenowy oraz sposób syntezy tego ligandu salphenowego - Google Patents
Ligand salphenowy oraz sposób syntezy tego ligandu salphenowegoInfo
- Publication number
- PL438656A1 PL438656A1 PL438656A PL43865621A PL438656A1 PL 438656 A1 PL438656 A1 PL 438656A1 PL 438656 A PL438656 A PL 438656A PL 43865621 A PL43865621 A PL 43865621A PL 438656 A1 PL438656 A1 PL 438656A1
- Authority
- PL
- Poland
- Prior art keywords
- tert
- butyl
- methyl
- hydroxyphenyl
- chloride
- Prior art date
Links
- HXFYGSOGECBSOY-UHFFFAOYSA-N 2-[[2-[(2-hydroxyphenyl)methylideneamino]phenyl]iminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NC1=CC=CC=C1N=CC1=CC=CC=C1O HXFYGSOGECBSOY-UHFFFAOYSA-N 0.000 title abstract 3
- 239000003446 ligand Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- -1 5-tert-butyl-3-formyl-2-hydroxyphenyl Chemical group 0.000 abstract 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 5
- WOIXERHXLOOLRS-UHFFFAOYSA-N 2-[(2-aminophenyl)iminomethyl]-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(C=NC=2C(=CC=CC=2)N)=C1O WOIXERHXLOOLRS-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 abstract 2
- OYRBMBWBIUDUKO-UHFFFAOYSA-N 5-tert-butyl-3-(chloromethyl)-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(CCl)=C(O)C(C=O)=C1 OYRBMBWBIUDUKO-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- RRIQVLZDOZPJTH-UHFFFAOYSA-N 3,5-di-tert-butyl-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=C(O)C(C(C)(C)C)=C1 RRIQVLZDOZPJTH-UHFFFAOYSA-N 0.000 abstract 1
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 abstract 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 abstract 1
- ZVCQQLGWGRTXGC-UHFFFAOYSA-N 5-tert-butyl-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC=C(O)C(C=O)=C1 ZVCQQLGWGRTXGC-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical class [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest ligand salphenowy O,N,N,O-donorowy, który jest asymetryczny, zaś w pozycji 3 jednego z jego dwóch pierścieni fenolanowych jest chlorek metyleno-(4-dimetyloaminopirydyniowy). Przedmiotem zgłoszenia jest także sposób otrzymywania ligandu salphenowego, który prowadzi się tak, że w pierwszym etapie 5-tert-butylo-2-hydroksybenzaldehyd poddawany jest chlorometylowaniu za pomocą formaliny o stężeniu procentowym 40% oraz stężonego kwasu solnego w temperaturze 70°C w czasie 48 godzin. Następnie otrzymany 5-tert-butylo-3-(chlorometylo)-2-hydroksybenzaldehyd poddawany jest reakcji DMAP w środowisku acetonitrylu w czasie 24 godzin i otrzymywany jest chlorek 1-[(5-tert-butyl-3-formylo-2-hydroksyfenylo)metylo]-4-(dimetylamino)pirydyn-1-iowy. W drugim etapie prowadzona jest reakcja pomiędzy o-fenylenodiaminą, a 3,5-di-tert-butylo-2-hydroksybenzaldehyd albo pomiędzy o-fenylenodiaminą, a 5-tert-butylo-3-(chlorometylo)-2-hydroksybenzaldehyd w obecności PTSA jako katalizatora w środowisku etanolu w czasie 12 godzin i otrzymywany jest 2-{[(2-aminofenylo)imino]metylo}-4,6-di-tert-butylofenol albo 2-{[(2-aminofenylo)imino]metylo}-4-tert-butylofenol. W trzecim etapie, w reaktorze wyposażonym w mieszadło, umieszcza się aktywowane sita molekularne oraz reagenty 2-{[(2-aminofenylo)imino]metylo}-4,6-di-tert-butylofenol oraz chlorek 1-[(5-tert-butyl-3-formylo-2-hydroksyfenylo)metylo]-4-(dimetylamino)pirydyn-1-iowy albo 2-{[(2-aminofenylo)imino]metylo}-4-tert-butylofenol oraz chlorek 1-{(5-tert-butyl-3-formylo-2-hydroksyfenylo)metylo]-4-(dimetylamino)pirydyn-1-iowym i prowadzi się reakcję 2-{[(2-aminofenylo)imino]metylo}-4,6-di-tert-butylofenolu z chlorkiem 1-[(5-tert-butyl-3-formylo-2-hydroksyfenylo)metylo]-4-(dimetylamino)pirydyn-1-iowym albo prowadzi się reakcję 2-{[(2-aminofenylo)imino]metylo}-4-tert-butylofenolu z chlorkiem 1-[(5-tert-butyl-3-formylo-2-hydroksyfenylo)metylo]-4-(dimetyloamino)pirydyn-1-iowym. Reakcje prowadzi się w obecności suchego metanolu, w atmosferze gazu obojętnego. Podczas prowadzenia reakcji zawartość reaktora miesza się. Po zakończeniu reakcji mieszaninę poreakcyjną przesącza się i przemywa się suchym metanolem. Metanol usuwa się z mieszaniny poreakcyjnej, a następnie pozostałość poreakcyjną rozpuszcza się w chlorku metylenu. Zyskany produkt oczyszcza się i uzyskuj się chlorek (5-tert-butylo-3-{[(2-{[(3,5-di-tert-butylo-2-hydroksyfenylo)metylideno]amino}fenylo)imino]metylo}-2-hydroksyfenylo)metanopirydyn-1-iowy albo chlorek (5-tert-butylo-3-{[(2-{[(5-ter-butylo-2-hydroksyfenylo)metylideno]amino}fenylo)imino]metylo}-2-hydroksyfenylo)metanopirydyn-1-iowy.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL438656A PL244191B1 (pl) | 2021-07-29 | 2021-07-29 | Ligand salphenowy oraz sposób syntezy tego ligandu salphenowego |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL438656A PL244191B1 (pl) | 2021-07-29 | 2021-07-29 | Ligand salphenowy oraz sposób syntezy tego ligandu salphenowego |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL438656A1 true PL438656A1 (pl) | 2023-01-30 |
| PL244191B1 PL244191B1 (pl) | 2023-12-11 |
Family
ID=85174241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL438656A PL244191B1 (pl) | 2021-07-29 | 2021-07-29 | Ligand salphenowy oraz sposób syntezy tego ligandu salphenowego |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL244191B1 (pl) |
-
2021
- 2021-07-29 PL PL438656A patent/PL244191B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL244191B1 (pl) | 2023-12-11 |
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