PL415664A1 - N-(5,6-dimethoxypyrimidyn-4-yl)-4-[(E)-phenylazo]benzenesulfonamide dyes and method for producing them - Google Patents
N-(5,6-dimethoxypyrimidyn-4-yl)-4-[(E)-phenylazo]benzenesulfonamide dyes and method for producing themInfo
- Publication number
- PL415664A1 PL415664A1 PL415664A PL41566415A PL415664A1 PL 415664 A1 PL415664 A1 PL 415664A1 PL 415664 A PL415664 A PL 415664A PL 41566415 A PL41566415 A PL 41566415A PL 415664 A1 PL415664 A1 PL 415664A1
- Authority
- PL
- Poland
- Prior art keywords
- hydroxyethyl
- amino
- benzenesulfonamide
- dimethoxypyrimidin
- phenylazo
- Prior art date
Links
- 239000000975 dye Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 title 1
- -1 5,6-dimethoxypyrimidin-4-yl Chemical group 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- HYVGFUIWHXLVNV-UHFFFAOYSA-N 2-(n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=CC=C1 HYVGFUIWHXLVNV-UHFFFAOYSA-N 0.000 abstract 1
- VIIZJXNVVJKISZ-UHFFFAOYSA-N 2-(n-methylanilino)ethanol Chemical compound OCCN(C)C1=CC=CC=C1 VIIZJXNVVJKISZ-UHFFFAOYSA-N 0.000 abstract 1
- PJSFRIWCGOHTNF-UHFFFAOYSA-N Sulphormetoxin Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC PJSFRIWCGOHTNF-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Zgłoszenie dotyczy barwników N-(5,6-dimetoksypyrimidyn-4-ilo)-4-[(E)-fenyloazo]benzenosulfonamidowych o wzorze ogólnym 1, w którym R oznacza grupę 2-hydroksyetylo(metylo)aminową, etylo(2-hydroksyetyloaminową) lub bis(2-hydroksyetylo)aminową, znajdujących zastosowanie w syntezie materiałów polimerowych i hybrydowych użytecznych w optycznym magazynowaniu i przetwarzaniu informacji oraz fotonice. Zgłoszenie ujawnia również sposób wytwarzania barwników N-(5,6-dimetoksypyrimidyn-4-ilo)-4-[(E)-fenyloazo]benzenosulfonamidowych o wzorze ogólnym 1, w którym R oznacza grupę 2-hydroksyetylo(metylo)aminową, etylo(2-hydroksyetyloaminową) lub bis(2-hydroksyetylo)aminową polegający tym, że 4-amino-N-(5,6-dimetoksypirymidyn-4-ilo)benzenosulfonamid poddaje się reakcji diazowania azotanem (III) sodu w mieszaninie stężonego kwasu solnego, wody i lodowatego kwasu octowego w temperaturze z zakresu od -5 do 10°C, po czym powstałą sól diazoniową w postaci chlorku 4-[(5,6-dimetoksypirymidyn-4-ilo)sulfamoilo]benzenodiazoniowego sprzęga się z aniliną wybraną spośród 2-(N-metyloanilino)etanolu, 2-(N-etyloanilino)etanolu lub 2-[N-(2-hydroksyetylo)anilino)]etanolu w temperaturze poniżej 10°C, a następnie otrzymany produkt wydziela się z mieszaniny reakcyjnej poprzez zobojętnienie i sączenie.The application relates to N- (5,6-dimethoxypyrimidin-4-yl) -4 - [(E) -phenylazo] benzenesulfonamide dyes of general formula 1, wherein R is 2-hydroxyethyl (methyl) amino, ethyl (2-hydroxyethylamino) ) or bis (2-hydroxyethyl) amino, which are used in the synthesis of polymeric and hybrid materials useful in optical storage and processing of information and photonics. The application also discloses a method for producing N- (5,6-dimethoxypyrimidin-4-yl) -4 - [(E) -phenylazo] benzenesulfonamide dyes of the general formula 1, wherein R is 2-hydroxyethyl (methyl) amino, ethyl ( 2-hydroxyethylamino) or bis (2-hydroxyethyl) amino in which 4-amino-N- (5,6-dimethoxypyrimidin-4-yl) benzenesulfonamide is subjected to a sodium nitrite diazotization reaction in a mixture of concentrated hydrochloric acid, water and glacial acetic acid at a temperature in the range of -5 to 10 ° C, after which the resulting diazonium salt in the form of 4 - [(5,6-dimethoxypyrimidin-4-yl) sulfamoyl] benzenediazonium chloride is coupled to aniline selected from 2- ( N-methylanilino) ethanol, 2- (N-ethylanilino) ethanol or 2- [N- (2-hydroxyethyl) anilino)] ethanol at a temperature below 10 ° C, and then the obtained product is separated from the reaction mixture by neutralization and filtration.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL415664A PL415664A1 (en) | 2015-12-30 | 2015-12-30 | N-(5,6-dimethoxypyrimidyn-4-yl)-4-[(E)-phenylazo]benzenesulfonamide dyes and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL415664A PL415664A1 (en) | 2015-12-30 | 2015-12-30 | N-(5,6-dimethoxypyrimidyn-4-yl)-4-[(E)-phenylazo]benzenesulfonamide dyes and method for producing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL415664A1 true PL415664A1 (en) | 2016-07-18 |
Family
ID=56370080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL415664A PL415664A1 (en) | 2015-12-30 | 2015-12-30 | N-(5,6-dimethoxypyrimidyn-4-yl)-4-[(E)-phenylazo]benzenesulfonamide dyes and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL415664A1 (en) |
-
2015
- 2015-12-30 PL PL415664A patent/PL415664A1/en unknown
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