CS264796B1 - 2-nitrophenol-4-n,4 -carboxyphenyl/sulphonamide and process for preparing them - Google Patents
2-nitrophenol-4-n,4 -carboxyphenyl/sulphonamide and process for preparing them Download PDFInfo
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- CS264796B1 CS264796B1 CS881303A CS130388A CS264796B1 CS 264796 B1 CS264796 B1 CS 264796B1 CS 881303 A CS881303 A CS 881303A CS 130388 A CS130388 A CS 130388A CS 264796 B1 CS264796 B1 CS 264796B1
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- Czechoslovakia
- Prior art keywords
- carboxyphenyl
- nitrophenol
- sulfonamide
- preparation
- sulphonamide
- Prior art date
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- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 18
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 3
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- -1 sulfonamide compound Chemical class 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řešení spadá do oblasti chemie organických barviv. Cílem řešení je sloučenina 2- -nitrofenol-4-(N,4'-karboxyfenyl)sulfonamidu a způsob její přípravy. Způsob přípravy 2-nitrofenol-4-(N,4'-karboxyfenyl)sulfonamidu vzorce I spočívá v tom, že se 2-nitrochlorbenzen- -4-(N,4'-karboxyfenyl)sulfonamid nechá reagovat s hydroxidem sodným ve vodném prostředí při teplotě 95 až 120 °C a při pH 11 až 14.The solution is in the field of organic chemistry dyes. The aim of the solution is compound 2- -nitrophenol-4- (N, 4'-carboxyphenyl) sulfonamide and the method of its preparation. Method of preparation 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfonamide of Formula I is that 2-nitrochlorobenzene Leaves -4- (N, 4'-carboxyphenyl) sulfonamide with aqueous sodium hydroxide at ambient temperature between 95 ° C and 120 ° C pH 11 to 14.
Description
(57) Řešení spadá do oblasti chemie organických barviv. Cílem řešení je sloučenina 2-nitrofenol-4-(N,4'-karboxyfenyl)sulfonamidu a způsob její přípravy. Způsob přípravy 2-nitrofenol-4-(N,4'-karboxyfenyl)sulfonamidu vzorce I(57) The solution falls within the field of organic dye chemistry. The object of the invention is a 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfonamide compound and a process for its preparation. A process for the preparation of 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfonamide of formula I
spočívá v tom, že se 2-nitrochlorbenzen-4-(N,4'-karboxyfenyl)sulfonamid nechá reagovat s hydroxidem sodným ve vodném prostředí při teplotě 95 až 120 °C a při pH 11 až 14.The method comprises reacting 2-nitrochlorobenzene-4- (N, 4'-carboxyphenyl) sulfonamide with sodium hydroxide in an aqueous medium at a temperature of 95-120 ° C and a pH of 11-14.
CS 264 796 BlCS 264 796 Bl
Vynález se týká 2-nitrofenol-4-(N,4'-karboxyfenol)sulfonamldu a způsobu jeho výroby..The present invention relates to 2-nitrophenol-4- (N, 4'-carboxyphenol) sulfonamide and to a process for its preparation.
Byla připravena sloučenina 2-nitrofenol-4-(N,4'-karboxyfenyl)sulfonamid, která může sloužit k dalším syntézám v oblasti chemie organických barviv.The compound 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfonamide was prepared, which can serve for further syntheses in the field of organic dye chemistry.
Způsob přípravy 2-nitrofenol-4-(N,4'-karboxyfenyl)sulfonamidu vzorce IA process for the preparation of 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfonamide of formula I
spočívá v tom, že se 2-nitroohlorbenzen-4-(N,4'-karboxyfenyl)sulfonamid nechá reagovat s hydroxidem sodným ve vodném prostředí při teplotě 95 až 120 °C s výhodou při teplotě 120 °C a pH 11 až 14. Průběh konverze je téměř kvantitativní, s minimem vedlejších chemických reakcí. Po izolaci se získá prakticky čistá látka vzorce I s teplotou tání 303 až 306 °C, s výtěžkem 99% teorie.characterized in that 2-nitro-chlorobenzene-4- (N, 4'-carboxyphenyl) sulfonamide is reacted with sodium hydroxide in an aqueous medium at a temperature of 95 to 120 ° C, preferably at a temperature of 120 ° C and a pH of 11 to 14. the conversion is almost quantitative, with a minimum of chemical side reactions. After isolation, a practically pure compound of formula I is obtained with a melting point of 303 DEG-306 DEG C. in a yield of 99% of theory.
Provedení podle vynálezu upřesňuje dále uvedený příklad.An embodiment of the invention is illustrated by the following example.
PříkladExample
35,7 g 100% 2-nitrochlorbenzen-4-(N,4'-karboxyfenyl)sulfonamidu (0,1 mol) se suspenduje ve 150 ml vody, přidá se 19,2 g hydroxidu sodného 100% ve formě roztoku o koncentraci c(NaOH) = 10 mol/1 a nechá se reagovat při teplotě 120 °C v laboratorním autoklávu při pH 11 až 14 po dobu 6 až 9 hodin.35.7 g of 100% 2-nitrochlorobenzene-4- (N, 4'-carboxyphenyl) sulfonamide (0.1 mol) is suspended in 150 ml of water, 19.2 g of sodium hydroxide 100% in the form of a c (NaOH) = 10 mol / l and reacted at 120 ° C in a laboratory autoclave at pH 11-14 for 6 to 9 hours.
Potom se reakčni směs ochladí na teplotu 20 až 30 °C a pomalu, za stálého míchání, se vykyselí kyselinou chlorovodíkovou o koncentraci c(HCl) = 9 mol/1 na pH 1.The reaction mixture was then cooled to 20-30 ° C and acidified slowly, with stirring, with c (HCl) = 9 mol / l hydrochloric acid to pH 1.
Získaný pevný podíl se izoluje filtrací. Filtrační koláč se promyje studenou vodou do ztráty kyselé reakce filtrátů.The resulting solid was collected by filtration. The filter cake is washed with cold water until the acidic reaction of the filtrates is lost.
Syntézou se získá 33,5 g 100% 2-nitrofenol-4-(N,4'-karboxyfenyl)sulfamidu o t.t. 303 až 306 °C.Synthesis yielded 33.5 g of 100% 2-nitrophenol-4- (N, 4'-carboxyphenyl) sulfamide, m.p. Mp 303-306 ° C.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881303A CS264796B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrophenol-4-n,4 -carboxyphenyl/sulphonamide and process for preparing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881303A CS264796B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrophenol-4-n,4 -carboxyphenyl/sulphonamide and process for preparing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS130388A1 CS130388A1 (en) | 1988-11-15 |
| CS264796B1 true CS264796B1 (en) | 1989-09-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS881303A CS264796B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrophenol-4-n,4 -carboxyphenyl/sulphonamide and process for preparing them |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS264796B1 (en) |
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1988
- 1988-03-01 CS CS881303A patent/CS264796B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS130388A1 (en) | 1988-11-15 |
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