PL422969A1 - Fluorine derivatives of azobenzene with polyamines and method for producing them - Google Patents
Fluorine derivatives of azobenzene with polyamines and method for producing themInfo
- Publication number
- PL422969A1 PL422969A1 PL422969A PL42296917A PL422969A1 PL 422969 A1 PL422969 A1 PL 422969A1 PL 422969 A PL422969 A PL 422969A PL 42296917 A PL42296917 A PL 42296917A PL 422969 A1 PL422969 A1 PL 422969A1
- Authority
- PL
- Poland
- Prior art keywords
- aminoethyl
- azobenzene
- polyamines
- tetrafluorobenzene
- difluorophenyl
- Prior art date
Links
- 229920000768 polyamine Polymers 0.000 title abstract 3
- 125000001153 fluoro group Chemical class F* 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 7
- -1 2,6-difluorophenyl Chemical group 0.000 abstract 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000007821 HATU Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000008423 fluorobenzenes Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- HGNOQXYYSVIUNS-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)-n-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCN(CCN)C(=O)OC(C)(C)C HGNOQXYYSVIUNS-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia są fluorowe pochodne azobenzenu z poliaminami o wzorze ogólnym 1, w którym R1 i R2 oznacza pochodną dietylotriaminy lub R1 oznacza pochodną dietylotriaminy a R2 oznacza wodór, w postaci: N,N'-Di-[2-N-(2-aminoetylo)aminoetylo]amid kwasu 2,2',6,6'-tetrafluorobenzeno-4,4'-dikarboksylowego oraz N-[2-N-(2-aminoetylo)aminoetylo]amid kwasu 4-(2,6-difluorofenylo)azo(2,6-difluoro)benzoesowego. Zgłoszenie obejmuje też sposób wytwarzania fluorowych pochodnych azobenzenu z poliaminami o wzorze ogólnym 1, w którym R1 i R2 oznacza pochodną dietylotriaminy lub R1 oznacza pochodną dietylotriaminy a R2 oznacza wodór. W sposobie tym do roztworu kwasu 4-(2,6-difluorofenylo)azo(2,6-difluoro)benzoesowego lub kwasu 2,2',6,6'- tetrafluorobenzeno-4,4'-dikarboksylowego w dimetyloformamidzie dodaje się DIPEA, HATU oraz N,N'-Di-Boc-dietylenotriaminę, następnie odblokowuje się grupy aminowe poprzez zawieszenie danego związku w dichlorometanie oraz dodanie kwasu trifluorooctowego, po czym rozpuszczalnik usuwa się pod zmniejszonym ciśnieniem, w efekcie czego, otrzymuje się: N-[2-N-(2-aminoetylo)aminoetylo]amid kwasu 4-(2,6-difluorofenylo)azo(2,6-difluoro)benzoesowego lub N,N'-Di-[2-N-(2-aminoetylo)aminoetylo]amid kwasu 2,2',6,6'-tetrafluorobenzeno-4,4'-dikarboksylowego w formie soli kwasu trifluorooctowego, w postaci pomarańczowego lub też czerwonego proszku.The subject of the application are fluorine derivatives of azobenzene with polyamines of the general formula 1, in which R1 and R2 is a diethyl triamine derivative or R1 is a diethyl triamine derivative and R2 is hydrogen, in the form: N, N'-Di- [2-N- (2-aminoethyl) ) 2,2 ', 6,6'-tetrafluorobenzene-4,4'-dicarboxylic acid and amino N- [2-N- (2-aminoethyl) aminoethyl] amide 4- (2,6-difluorophenyl) azo (2,6-difluoro) benzoic acid. The application also includes a process for the preparation of fluorobenzenes of azobenzene with polyamines of general formula 1, in which R 1 and R 2 is a diethyl triamine derivative or R 1 is a diethyl triamine derivative and R 2 is hydrogen. In this process, DIPEA is added to a solution of 4- (2,6-difluorophenyl) azo (2,6-difluoro) benzoic acid or 2,2 ', 6,6'-tetrafluorobenzene-4,4'-dicarboxylic acid in dimethylformamide. HATU and N, N'-Di-Boc-diethylenetriamine, then the amino groups are unblocked by suspending the compound in dichloromethane and adding trifluoroacetic acid, after which the solvent is removed under reduced pressure, resulting in: N- [2- 4- (2,6-difluorophenyl) azo (2,6-difluoro) benzoic acid or N, N'-Di- [2-N- (2-aminoethyl) aminoethyl] amide N- (2-aminoethyl) aminoethyl] amide 2,2 ', 6,6'-tetrafluorobenzene-4,4'-dicarboxylic acid in the form of the trifluoroacetic acid salt, in the form of an orange or red powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422969A PL231878B1 (en) | 2017-09-26 | 2017-09-26 | Fluorine derivatives of azobenzene with polyamines and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL422969A PL231878B1 (en) | 2017-09-26 | 2017-09-26 | Fluorine derivatives of azobenzene with polyamines and method for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL422969A1 true PL422969A1 (en) | 2018-06-04 |
| PL231878B1 PL231878B1 (en) | 2019-04-30 |
Family
ID=62223420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL422969A PL231878B1 (en) | 2017-09-26 | 2017-09-26 | Fluorine derivatives of azobenzene with polyamines and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL231878B1 (en) |
-
2017
- 2017-09-26 PL PL422969A patent/PL231878B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL231878B1 (en) | 2019-04-30 |
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