CS264929B1 - 2-nitrophenyl-4-/n-carboxyphenyl-sulphonamid and process for preparing thereof - Google Patents
2-nitrophenyl-4-/n-carboxyphenyl-sulphonamid and process for preparing thereof Download PDFInfo
- Publication number
- CS264929B1 CS264929B1 CS881313A CS131388A CS264929B1 CS 264929 B1 CS264929 B1 CS 264929B1 CS 881313 A CS881313 A CS 881313A CS 131388 A CS131388 A CS 131388A CS 264929 B1 CS264929 B1 CS 264929B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carboxyphenyl
- sulfonamide
- nitrophenyl
- nitrophenol
- sulphonamid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 18
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 12
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- -1 2-carboxyphenyl Chemical group 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 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
- 125000000896 monocarboxylic acid group Chemical group 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
- 239000000463 material Substances 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
- 238000004448 titration Methods 0.000 description 1
Landscapes
- 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,2 '-karboxyfenyl)- sulfonamid a způsob jeho přípravy. Způsob přípravy 2-nitrofenyl-4-(N,2'-karboxyfenyl)sulfonamidu vzorce I OH no2 O COOH S02— NH---- (I) spočívá v tom, že se 2-nitrochlorbenzen- -4- (N,2'-karboxyfenyl)sulfonamid nechá reagovat s hydroxidem sodným ve vodném prostředí při teplotě 98 až 100 °C a pH 11 až 14.The solution is in the field of organic chemistry dyes. The goal of the solution is the compound 2-Nitrophenol-4- (N, 2'-carboxyphenyl) - sulfonamide and a process for its preparation. Way to prepare 2-nitrophenyl-4- (N, 2'-carboxyphenyl) sulfonamide of Formula I OH no2 O COOH S02 - NH ---- (I) is that 2-nitrochlorobenzene Leaves -4- (N, 2'-carboxyphenyl) sulfonamide with aqueous sodium hydroxide at a temperature of 98 to 100 ° C and pH 11 to 14.
Description
Vynález se týká 2-nitrofenol-4-(N,2'-karboxyfenyl)sulfonamidu a způsobu jeho výroby.The invention relates to 2-nitrophenol-4- (N, 2'-carboxyphenyl) sulfonamide and to a process for its preparation.
Byla připravena sloučenina 2-nitrofenol-4-(N,2-karboxyfenyl)sulfonamid, která může sloužit k dalším syntézám v oblasti chemie organických barviv.The compound 2-nitrophenol-4- (N, 2-carboxyphenyl) sulfonamide was prepared, which can serve for further syntheses in the field of organic dye chemistry.
Způsob přípravy 2-nitrofenol-4-(N,2-karboxyfenyl)sulfonamidu vzorce IA process for the preparation of 2-nitrophenol-4- (N, 2-carboxyphenyl) sulfonamide of formula I
OHOH
spočívá v tom, že se 2-nitrochlorbenzen-4-(N,2-karboxyfenyl)sulfonamid nechá reagovat s hydroxidem sodným ve vodném prostředí při teplotě 95 až 105 °C s výhodou při teplotě 98 až 100 °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 208 až 209 °C, s výtažkem 98 % teorie.characterized in that 2-nitrochlorobenzene-4- (N, 2-carboxyphenyl) sulfonamide is reacted with sodium hydroxide in an aqueous medium at a temperature of 95 to 105 ° C, preferably at a temperature of 98 to 100 ° C and a pH of 11 to 14. The conversion process 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 208 DEG-209 DEG C. in a yield of 98% of theory.
Titrací této látky hydroxidem sodným ve vodném prostředí s využitím potenciometrické indikace byla stanovena relativní molární hmotnost 338.Titration of this material with sodium hydroxide in an aqueous medium using potentiometric indication gave a relative molar mass of 338.
Provedení podle vynálezu upřesňuje dále uvedený příklad.An embodiment of the invention is illustrated by the following example.
P ř í k 1 a dExample 1 a d
35,7 g 100% 2-nitrochlorbenzen-4-(K,2'-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 98 až 100 °C, pH 11 až 14 a po dobu 6 až 9 hodin.35.7 g of 100% 2-nitrochlorobenzene-4- (K, 2'-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 98-100 ° C, pH 11-14 and for 6-9 hours.
Potom se reakční 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 teplou vodou do ztráty kyselé reakce filtrátů.The resulting solid was collected by filtration. The filter cake is washed with warm water until the acidic reaction of the filtrates is lost.
Syntézou se získá 33,1 g 100% 2-nitrofenol-4-(N,2'-karboxyfenyl)sulfonamidu o t.t.Synthesis yielded 33.1 g of 100% 2-nitrophenol-4- (N, 2'-carboxyphenyl) sulfonamide, m.p.
208 až 209 °C.Mp 208-209 ° C.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881313A CS264929B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrophenyl-4-/n-carboxyphenyl-sulphonamid and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881313A CS264929B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrophenyl-4-/n-carboxyphenyl-sulphonamid and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS131388A1 CS131388A1 (en) | 1988-12-15 |
| CS264929B1 true CS264929B1 (en) | 1989-09-12 |
Family
ID=5347208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS881313A CS264929B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrophenyl-4-/n-carboxyphenyl-sulphonamid and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS264929B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113767913A (en) * | 2021-08-13 | 2021-12-10 | 上海应用技术大学 | Application of a kind of 2-[(4-chloro-3-nitrophenyl) sulfonamido] benzoic acid in preparing insect growth regulator |
-
1988
- 1988-03-01 CS CS881313A patent/CS264929B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113767913A (en) * | 2021-08-13 | 2021-12-10 | 上海应用技术大学 | Application of a kind of 2-[(4-chloro-3-nitrophenyl) sulfonamido] benzoic acid in preparing insect growth regulator |
Also Published As
| Publication number | Publication date |
|---|---|
| CS131388A1 (en) | 1988-12-15 |
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