PL422411A1 - Method for obtaining symmetric 2,6-disubstituted 1,4,5,8- naphthalenediimides - Google Patents

Method for obtaining symmetric 2,6-disubstituted 1,4,5,8- naphthalenediimides

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Publication number
PL422411A1
PL422411A1 PL422411A PL42241117A PL422411A1 PL 422411 A1 PL422411 A1 PL 422411A1 PL 422411 A PL422411 A PL 422411A PL 42241117 A PL42241117 A PL 42241117A PL 422411 A1 PL422411 A1 PL 422411A1
Authority
PL
Poland
Prior art keywords
dibromo
naphthalene diimide
amount
naphthalene
molar equivalent
Prior art date
Application number
PL422411A
Other languages
Polish (pl)
Other versions
PL232560B1 (en
Inventor
Sonia Kotowicz
Mateusz Korzec
Ewa Schab-Balcerzak
Original Assignee
Uniwersytet Śląski
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.)
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Publication date
Application filed by Uniwersytet Śląski filed Critical Uniwersytet Śląski
Priority to PL422411A priority Critical patent/PL232560B1/en
Publication of PL422411A1 publication Critical patent/PL422411A1/en
Publication of PL232560B1 publication Critical patent/PL232560B1/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Przedmiotem zgłoszenia jest sposób otrzymywania 2,6-dialkino-1,4,5,8-naftalenodiimidów, który charakteryzuje się tym że, 2,6-dibromo-1,4,5,8-naftalenodiimid w ilości jednego równoważnika molowego, PdCl2 nie mniej niż 1 mg, proszku miedzi elektrolitycznej nie mniej niż 1 mg, zasady organicznej w ilości równej co najmniej jednemu równoważnikowi molowemu na równoważnik 2,6-dibromo-1,4,5,8-naftalenodiimidu, polarnego rozpuszczalnika lub ich mieszaniny w ilości nie niniejszej niż 5 cm3 na 0,5 mmol 2,6-dibromo-1,4,5,8-naftalenodiimidu oraz alkinu terminalnego w ilości równej 1,1 równoważnika molowego na równoważnik 2,6-dibromo-1,4,5,8-naftalenodiimidu, intensywnie miesza się i ogrzewa, korzystnie do 60°C, w czasie od 0,5 do 24 godzin, korzystnie 1 godzinę, po czym mieszaninę wymraża się w łaźni lodowej lub zamrażarce intensywnie mieszając, przez co najmniej 0,5 godziny, następnie wydzielony produkt odsącza się grawitacyjnie lub pod zmniejszonym ciśnieniem i przemywa acetonem, a następnie oczyszcza znanymi metodami korzystnie w procesie krystalizacji, ekstrakcji lub z węglem aktywnym.The subject of the application is a method for obtaining 2,6-dialkino-1,4,5,8-naphthalene diimides, which is characterized in that, 2,6-dibromo-1,4,5,8-naphthalene diimide in the amount of one molar equivalent, PdCl2 is not less than 1 mg, electrolytic copper powder not less than 1 mg, organic base in an amount equal to at least one molar equivalent per equivalent of 2,6-dibromo-1,4,5,8-naphthalene diimide, a polar solvent or a mixture thereof in an amount of of this than 5 cm3 per 0.5 mmol 2,6-dibromo-1,4,5,8-naphthalene diimide and a terminal alkyne equal to 1.1 molar equivalent per equivalent of 2,6-dibromo-1,4,5,8 - naphthalene diimide, vigorously mixed and heated, preferably to 60 ° C, for 0.5 to 24 hours, preferably 1 hour, after which the mixture is frozen in an ice bath or freezer with vigorous stirring for at least 0.5 hour, then the separated product is filtered by gravity or under reduced pressure em and washed with acetone, followed by purification by known methods preferably in a crystallization, extraction or activated carbon process.

PL422411A 2017-07-31 2017-07-31 Method for obtaining symmetric 2,6-disubstituted 1,4,5,8- naphthalenediimides PL232560B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL422411A PL232560B1 (en) 2017-07-31 2017-07-31 Method for obtaining symmetric 2,6-disubstituted 1,4,5,8- naphthalenediimides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL422411A PL232560B1 (en) 2017-07-31 2017-07-31 Method for obtaining symmetric 2,6-disubstituted 1,4,5,8- naphthalenediimides

Publications (2)

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PL422411A1 true PL422411A1 (en) 2019-02-11
PL232560B1 PL232560B1 (en) 2019-06-28

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PL422411A PL232560B1 (en) 2017-07-31 2017-07-31 Method for obtaining symmetric 2,6-disubstituted 1,4,5,8- naphthalenediimides

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101066934A (en) * 2007-06-06 2007-11-07 北京化工大学 Chiral beta-keto diimide ligand compound and its prepn and application

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101066934A (en) * 2007-06-06 2007-11-07 北京化工大学 Chiral beta-keto diimide ligand compound and its prepn and application

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PARK KYUNG-HO, MARSHALL, W.J.J., THE JOURNAL OF ORGANIC CHEMISTRY, 2005 *
S-L. SURARU, F. WURTHNER, A JOURNAL OF THE GESSELSCHAFT DEUTSCHER CHEMIKER, 2014 *

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Publication number Publication date
PL232560B1 (en) 2019-06-28

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