PL223363B1 - Photochromic monomer azobenzene -- 2-methyl-prop-2-enoate4[€-(4-hydroxyphenyl)diazenyl]-N-(5-methyl-3-yl)-benzenesulfonamide, and its production process - Google Patents
Photochromic monomer azobenzene -- 2-methyl-prop-2-enoate4[€-(4-hydroxyphenyl)diazenyl]-N-(5-methyl-3-yl)-benzenesulfonamide, and its production processInfo
- Publication number
- PL223363B1 PL223363B1 PL407229A PL40722914A PL223363B1 PL 223363 B1 PL223363 B1 PL 223363B1 PL 407229 A PL407229 A PL 407229A PL 40722914 A PL40722914 A PL 40722914A PL 223363 B1 PL223363 B1 PL 223363B1
- Authority
- PL
- Poland
- Prior art keywords
- benzenesulfonamide
- hydroxyphenyl
- diazenyl
- methylisoxazol
- methyl
- Prior art date
Links
- 239000000178 monomer Substances 0.000 title claims description 18
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- -1 5-methylisoxazol-3-yl Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical class O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 claims description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000005457 ice water Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000005395 methacrylic acid group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical group CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NRJPVIOTANUINF-UHFFFAOYSA-N chembl2204743 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1 NRJPVIOTANUINF-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest fotochromowy monomer azobenzenowy 2-metyloprop-2-enianThe present invention relates to 2-methylprop-2-enate photochromic azobenzene monomer
4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu znajdujący zastosowanie do otrzymywania polimerów i kopolimerów o właściwościach fotochromowych, zmieniających właściwości pod wpływem światła, które mogą być stosowane w optycznym zapisie i przetwarzaniu informacji.4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide applicable for the preparation of polymers and copolymers with photochromic properties, changing properties under the influence of light, which can be used in optical saving and processing information.
Przedmiotem wynalazku jest również sposób wytwarzania fotochromowego monomeru azobenzenowego 2-metyloprop-2-enian 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu.The invention also relates to a process for the preparation of 4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide photochromic azobenzene monomer 2-methylprop-2-enate.
Znany jest z polskiego opisu patentowego PL190968 sposób wytwarzania nowych, chromoforowych monomerów metakrylowych zawierających heteroaromatyczne ugrupowania: tiazol-2-ylowe, pirymidyn-2-ylowe, 2,6-dimetylopirymidyn-4-ylowe lub 5-metyloizoksazol-3-ylowe, znamienny tym, że N-podstawione ugrupowaniem heteroaromatycznym w grupie sulfonamidowej 4-aminobenzenosulfonamidy, z ugrupowaniem tiazol-2-ylowym, pirymidyn-2-ylowym, 2,6-dimetylopirymidyn-4-ylowym lub 5-metyloizoksazol-3-ylowym, poddaje się reakcji diazowania, w środowisku stężonego kwasu octowego, po czym otrzymane sole diazoniowe poddaje się reakcji sprzęgania z N-alkilo-N-(metakryloiloksy)-etyloaniliną, w której grupą alkilową jest CH3-, C2H5- lub C4H9, w środowisku mieszaniny stężonego kwasu octowego z 2-metoksy- lub 2-etoksyetanolem, w obecności octanu sodowego i w temperaturze od 0 do +5°C, a otrzymane chromoforowe monomery metakrylowe oczyszcza się przez krystalizację z mieszaniny dimetyloformamidu i wody.There is known from the Polish patent description PL190968 a method of producing new, chromophore methacrylic monomers containing heteroaromatic groups: thiazol-2-yl, pyrimidin-2-yl, 2,6-dimethylpyrimidin-4-yl or 5-methylisoxazol-3-yl, characterized by that the N-substituted heteroaromatic moiety in the sulfonamide group of 4-aminobenzenesulfonamides with a thiazol-2-yl, pyrimidin-2-yl, 2,6-dimethylpyrimidin-4-yl or 5-methylisoxazol-3-yl moiety is subjected to a diazotization reaction in a concentrated acetic acid medium, then the obtained diazonium salts are coupled with N-alkyl-N- (methacryloyloxy) -ethylaniline in which the alkyl group is CH 3 -, C 2 H 5 - or C 4 H 9 , in the medium of a mixture of concentrated acetic acid with 2-methoxy or 2-ethoxyethanol, in the presence of sodium acetate and at a temperature of 0 to + 5 ° C, and the obtained methacrylic chromophore monomers are purified by crystallization from a mixture of dimethylformamide and water.
W publikacji F. A. Nicolescu, V. V. Jerca, C. Draghici, D. M. Vuluga, D. S. Vasilescu Designed Monomers and Polymers 12 (2009) 553-563 opisano sposób otrzymywania monomerów azobenzenowych, polegający na reakcji azo pochodnych fenolu z podstawnikami takimi jak: grupa nitrowa, nitrylowa z chlorkiem kwasu metakrylowego. Reakcje prowadzono w roztworze stosując dichlorometan jako rozpuszczalnik, w atmosferze argonu, w obecności trietyloaminy.The publication FA Nicolescu, VV Jerca, C. Draghici, DM Vuluga, DS Vasilescu Designed Monomers and Polymers 12 (2009) 553-563 describes a method of obtaining azobenzene monomers, consisting in the reaction of azo derivatives of phenol with substituents such as: nitro, nitrile group with methacrylic acid chloride. Reactions were carried out in solution using dichloromethane as solvent under argon in the presence of triethylamine.
Z publikacji Q. Tang, X. Meng, H. Jiang, T. Zhou, C. Gong, X. Fu, S. Shi Journal of Material Chemistry 20 (2010) 9133-9139 znany jest monomer metakrylowy [4-[(E)-(4-aminofenylo)azo]fenylo]-2-metyloprop-2-enian o właściwościach fotochromowych. Opisany w publikacji sposób syntezy m onomeru polega na otrzymaniu 4-nitro-4'-hydroksyazobenzenu, który następnie poddaje się reakcji z chlorkiem kwasu metakrylowego. W kolejnym etapie podstawnik nitrowy poddaje się redukcji, otrz ymując grupę aminową. W dalszym etapie monomer ten posłużył do otrzymania polimerowych nanocząstek wrażliwych na światło i pH.From Q. Tang, X. Meng, H. Jiang, T. Zhou, C. Gong, X. Fu, S. Shi Journal of Material Chemistry 20 (2010) 9133-9139 a methacrylic monomer [4 - [(E ) - (4-aminophenyl) azo] phenyl] -2-methylprop-2-enoate with photochromic properties. The monomer synthesis method described in the publication consists in obtaining 4-nitro-4'-hydroxyazobenzene, which is then reacted with methacrylic acid chloride. In the next step, the nitro substituent is reduced to give an amino group. In a further step, this monomer was used to obtain polymeric nanoparticles sensitive to light and pH.
W publikacji L. Fang, S. Chen, Y. Zhang, H. Zhang Journal of Material Chemistry 21 (2011) 2320-2329 opisano sposób synezy [4-[(E)-4-pirymidynylazo]fenylo] 2-metylprop-2-enianu, polegający na reakcji 4-(4-hydroksyfenylolazo)pirydyny z bezwodnikiem metakrylowym w roztworze osuszonego tetrahydrofuranu, w obecności 4-dimetyloaminopirydyny i trietyloaminy. Monomer ten został zastosowany do przygotowania mikrosfer polimerowych o właściwościach fotochromowych.The publication of L. Fang, S. Chen, Y. Zhang, H. Zhang Journal of Material Chemistry 21 (2011) 2320-2329 describes the synthesis of [4 - [(E) -4-pyrimidinylzo] phenyl] 2-methylprop-2 -enate, by reacting 4- (4-hydroxyphenyl lazo) pyridine with methacrylic anhydride in a solution of dried tetrahydrofuran in the presence of 4-dimethylaminopyridine and triethylamine. This monomer was used to prepare polymer microspheres with photochromic properties.
Dotychczas nie zostały opisane w literaturze fotochromowe monomery azobenzenowe ani sposób ich wytwarzania.So far, neither the photochromic azobenzene monomers nor the method of their preparation have been described in the literature.
Istotą rozwiązania według wynalazku jest fotochromowy monomer azobenzenowy 2-metyloprop-2-enian 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamid o wzorze 1, będący pochodną 4-amino-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu.The essence of the solution according to the invention is the photochromic azobenzene monomer 2-methylprop-2-enate 4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide of formula 1, which is a derivative of 4- amino-N- (5-methylisoxazol-3-yl) benzenesulfonamide.
Istotą wynalazku jest również sposób wytwarzania fotochromowego monomeru azobenzenowego 2-metyloprop-2-enian 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu o wzorze 1, będącego pochodną 4-amino-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu polegający na tym, że bezwodnik kwasu metakrylowego poddaje się reakcji z 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidem, przy czym reakcję prowadzi się w rozpuszczalniku będącym pirydyną i przy użyciu katalizatora w postaci 4-dimetyloaminopirydyny oraz w środowisku gazu inertnego.The essence of the invention is also a process for the preparation of the photochromic azobenzene monomer 4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide of formula 1, which is a derivative of 4 -amino-N- (5-methylisoxazol-3-yl) benzenesulfonamide by reacting methacrylic acid anhydride with 4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3) -yl) benzenesulfonamide, and the reaction is carried out in a pyridine solvent and with the aid of a 4-dimethylaminopyridine catalyst and in an inert gas environment.
Korzystnie reakcję prowadzi się w roztworze tak aby stosunek 4-[(E)-(4-hydroksyfenylo)dia3 zenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu do pirydyny wynosił od 0,01 mola w 20 cm 3 bezwodnej pirydyny do 0,01 mola w 35 cm bezwodnej pirydyny.Preferably, the reaction is carried out in solution such that the ratio of 4 - [(E) - (4-hydroxyphenyl) diasthenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide to pyridine is 0.01 mol in 20 cm 3 of anhydrous pyridine to 0.01 mole in 35 cm of anhydrous pyridine.
Korzystnie jako gaz inertny stosuje się azot lub argon.Preferably, nitrogen or argon is used as the inert gas.
Korzystnie reakcję prowadzi się mieszając mieszaninę reakcyjną w temperaturze pokojowej przez czas 48 godzin.Preferably the reaction is carried out by stirring the reaction mixture at room temperature for 48 hours.
PL 223 363 B1PL 223 363 B1
Korzystnie otrzymany produkt wydziela się przez wytrącanie z wody lub mieszaniny wodnolodowej.Preferably the product obtained is separated by precipitation from water or a water / ice mixture.
Przedmiot wynalazku przedstawiony jest w przykładach jego wykonania oraz wzorem 1.The subject of the invention is presented in the examples of its implementation and the formula 1.
P r z y k ł a d 1P r z k ł a d 1
Sposób wytwarzania monomeru azobenzenowego 2-metyloprop-2-enianu 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu pochodnego 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu o wzorze 1.Process for the preparation of azobenzene monomer 4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide derived from 4 - [(E) - (4-hydroxyphenyl) ) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide of formula 1.
W kolbie okrągłodennej umieszcza się 3,72 g (0,01 mol) 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ylo)benzenosulfonoamidu i 35 cm bezwodnej pirydyny i miesza się do całkowitego rozpuszczenia osadu. Następnie porcjami dodaje się 1,96 g (12,7 mmol) bezwodnika kwasu metakrylowego i 0,03 g (0,227 mmol) 4-dimetyloaminopirydyny. Kolbę przedmuchuje się azotem i miesza w temperaturze pokojowej przez 48 godzin. Po tym czasie mieszaninę reakcyjną wylewa się do mieszaniny wodno-lodowej. Wytrącony pomarańczowy osad odsącza się, przemywa kilkukrotnie wodą destylowaną i suszy w temperaturze 30-40°C. Wydajność produktu otrzymanego tą metodą wynosi 88%.3.72 g (0.01 mol) of 4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide and 35 cm of anhydrous pyridine are placed in a round bottom flask and mixed with until the precipitate is completely dissolved. Then 1.96 g (12.7 mmol) of methacrylic anhydride and 0.03 g (0.227 mmol) of 4-dimethylaminopyridine are added portionwise. The flask was purged with nitrogen and stirred at room temperature for 48 hours. At this time, the reaction mixture was poured into an ice-water mixture. The precipitated orange solid is filtered off, washed several times with distilled water and dried at 30-40 ° C. The yield of the product obtained by this method is 88%.
1HNMR (rozpuszczalnik DMSO-d6, wzorzec TMS): 2,01 (s, 3H -CH3); 2,26 (s, 3H, -CH3 w pierścieniu metyloizoksazolowym); 5,94 (s, 1H, -CH2); 6,12 (s, 1H, -CH2); 6,32 (s, 1H, proton w pierścieniu metyloizoksazolowym); 7,45 (m, 2H, protony w pierścieniu fenylowym w pozycji orto do grupy metakrylowej); 7,97 (m, 2H, protony pierścienia fenylowego w pozycji meta do grupy metakrylowej); 7,99 (m, 2H, protony pierścienia fenylowego w pozycji orto do grupy N=N); 8,01 (d, 2H, protony pierścienia fenylowego w pozycji meta do grupy N=N). 1 HNMR (DMSO-d 6 solvent, TMS pattern): 2.01 (s, 3H -CH 3 ); 2.26 (s, 3H, -CH 3 in ring metyloizoksazolowym); 5.94 (s, 1H, CH 2); 6.12 (s, 1H, CH 2); 6.32 (s, 1H, proton on the methyl isoxazole ring); 7.45 (m, 2H, protons in the phenyl ring ortho to the methacrylic group); 7.97 (m, 2H, phenyl ring protons meta to the methacrylic group); 7.99 (m, 2H, the phenyl ring protons ortho to the N = N group); 8.01 (d, 2H, phenyl ring protons meta to N = N).
P r z y k ł a d 2P r z k ł a d 2
Sposób wytwarzania monomeru azobenzenowego 2-metyloprop-2-enianu 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu pochodnego 4-[(E)-(4-hydroksyfenylo)diazenylo]-N-(5-metyloizoksazol-3-ilo)benzenosulfonoamidu o wzorze 1 jak w przykładzie 1, przy czym kolbę przedmuchuje się argonem.Process for the preparation of azobenzene monomer 4 - [(E) - (4-hydroxyphenyl) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide derived from 4 - [(E) - (4-hydroxyphenyl) ) diazenyl] -N- (5-methylisoxazol-3-yl) benzenesulfonamide of formula 1 as in Example 1, the flask purged with argon.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| PL407229A PL223363B1 (en) | 2014-02-18 | 2014-02-18 | Photochromic monomer azobenzene -- 2-methyl-prop-2-enoate4[€-(4-hydroxyphenyl)diazenyl]-N-(5-methyl-3-yl)-benzenesulfonamide, and its production process |
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| Application Number | Priority Date | Filing Date | Title |
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| PL407229A PL223363B1 (en) | 2014-02-18 | 2014-02-18 | Photochromic monomer azobenzene -- 2-methyl-prop-2-enoate4[€-(4-hydroxyphenyl)diazenyl]-N-(5-methyl-3-yl)-benzenesulfonamide, and its production process |
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| Publication Number | Publication Date |
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| PL407229A1 PL407229A1 (en) | 2014-11-24 |
| PL223363B1 true PL223363B1 (en) | 2016-10-31 |
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