PL406418A1 - Amine derivative of azobenzene and the method of its production - Google Patents
Amine derivative of azobenzene and the method of its productionInfo
- Publication number
- PL406418A1 PL406418A1 PL406418A PL40641813A PL406418A1 PL 406418 A1 PL406418 A1 PL 406418A1 PL 406418 A PL406418 A PL 406418A PL 40641813 A PL40641813 A PL 40641813A PL 406418 A1 PL406418 A1 PL 406418A1
- Authority
- PL
- Poland
- Prior art keywords
- azobenzene
- aminoethyl
- trifluoroacetic acid
- added
- amino derivative
- Prior art date
Links
- -1 Amine derivative of azobenzene Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- RYMHZBAYPLCCAC-UHFFFAOYSA-N 4-phenyldiazenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1N=NC1=CC=CC=C1 RYMHZBAYPLCCAC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000015654 memory Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- KQXGYFNJIMVFDT-UHFFFAOYSA-N tert-butyl n-[2-(2-aminoethylamino)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCNCCN KQXGYFNJIMVFDT-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem wynalazku jest aminowa pochodna azobenzenu w postaci N-[N'-(2'-aminoetylo)-2-aminoetylo]azobenzeno-4- karboksyamidu o wzorze 1 znajdująca zastosowanie jako molekularny przełącznik stosowany w biologii molekularnej, inżynierii materiałowej, chemicznej diagnostyce medycznej oraz jako składnik barwników czy też jako element pamięci optycznych. Sposób wytwarzania aminowej pochodnej azobenzenu w postaci N-[N'-(2'-aminoetylo)-2-aminoetylo]azobenzeno-4- karboksyamidu o wzorze 1 polega na tym, że do N1-Boc-2,2'-iminodietylaminy dodaje się trietyloaminy, przez mieszaninę przepuszcza się azot i całość ochładza się do 0°C, po czym wkrapla się chlorek azobenzeno-4-karbonylowy w obecności bezwodnego dichlorometanu, a następnie otrzymaną N-Boc aminową pochodną azobenzenu umieszcza się w dichlorometanie i dodaje się kwasu trifluorooctowego, otrzymany roztwór miesza się przez 2 godziny, po czym odparowuje się rozpuszczalnik oraz kwas trifluorooctwy pod zmniejszonym ciśnieniem, w wyniku czego otrzymuje się aminową pochodna azobenzenu o wzorze w formie jego soli kwasu trifluorooctowego, w postaci pomarańczowego proszku.The subject of the invention is an amino derivative of azobenzene in the form of N- [N '- (2'-aminoethyl) -2-aminoethyl] azobenzene-4-carboxamide of formula 1, which is used as a molecular switch used in molecular biology, material engineering, chemical medical diagnostics and as a component of dyes or as an element of optical memories. The method for producing the amine derivative of azobenzene in the form of N- [N '- (2'-aminoethyl) -2-aminoethyl] azobenzene-4-carboxamide of formula 1 consists in adding N1-Boc-2,2'-iminodiethylamine triethylamine, nitrogen is bubbled through the mixture and the whole is cooled to 0 ° C, then azobenzene-4-carbonyl chloride is added dropwise in the presence of anhydrous dichloromethane, and then the N-Boc amino derivative of azobenzene is added to dichloromethane and trifluoroacetic acid is added, the resulting solution is stirred for 2 hours, then the solvent and trifluoroacetic acid are evaporated under reduced pressure to give the amino derivative of azobenzene in the form of its trifluoroacetic acid salt as an orange powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406418A PL221867B1 (en) | 2013-12-09 | 2013-12-09 | Amine derivative of azobenzene and a method for its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406418A PL221867B1 (en) | 2013-12-09 | 2013-12-09 | Amine derivative of azobenzene and a method for its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL406418A1 true PL406418A1 (en) | 2014-07-07 |
| PL221867B1 PL221867B1 (en) | 2016-06-30 |
Family
ID=51063170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL406418A PL221867B1 (en) | 2013-12-09 | 2013-12-09 | Amine derivative of azobenzene and a method for its preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221867B1 (en) |
-
2013
- 2013-12-09 PL PL406418A patent/PL221867B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221867B1 (en) | 2016-06-30 |
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