CS265433B1 - 2-nitrochlorbenzen-4-/n,4-carboxyphenyl/sulphamide and process for preparing them - Google Patents
2-nitrochlorbenzen-4-/n,4-carboxyphenyl/sulphamide and process for preparing them Download PDFInfo
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- CS265433B1 CS265433B1 CS881302A CS130288A CS265433B1 CS 265433 B1 CS265433 B1 CS 265433B1 CS 881302 A CS881302 A CS 881302A CS 130288 A CS130288 A CS 130288A CS 265433 B1 CS265433 B1 CS 265433B1
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- CS
- Czechoslovakia
- Prior art keywords
- nitrochlorobenzene
- carboxyphenyl
- sulfonamide
- preparation
- formula
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 title 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 9
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 7
- 229960004050 aminobenzoic acid Drugs 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 18
- 238000002360 preparation method Methods 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- -1 4-carboxyphenyl Chemical group 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract description 3
- 239000012736 aqueous medium Substances 0.000 abstract description 3
- 239000000872 buffer Substances 0.000 abstract description 3
- 239000000975 dye Substances 0.000 abstract description 3
- 239000000049 pigment Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 230000000903 blocking effect Effects 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000004941 influx Effects 0.000 description 2
- 238000005187 foaming Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řešeni spadá do oblasti chemie organických barviv a pigmentů a přípravků pro protimolovou ochranu. Cílem řešení je sloučenina 2-nitrochlorbenzen-4-(N,4’-karboxyfenyl)sulfonamid a způsob její přípravy. Způsob přípravy 2-nitrochlorbenzen-4-(N, 4 1-karboxyfenyl)- sulfonamidu vzorce I Cl LO. no2 (I) so2-nh spočívá v tom, že se vodorozpustná sůl kyseliny 4-aminobenzoové nechá reagovat ve vodném prostředí a 2-nitrochlorbenzen-2-sulfonylchloridem při pH 2 až 9, s výhodou pH 5 až 7. Oblast výhodného pH se ve stanoveném rozmezí udržuje při syntéze regulačním pH-metrem s blokací nátoku hydroxidu sodného nebo se pracuje v prostředí vhodného pufru - např. hydrogenuhličitanu.The solution falls within the field of organic chemistry dyes and pigments and preparations for antimoles protection. The goal of the solution is the compound 2-nitrochlorobenzene-4- (N, 4'-carboxyphenyl) sulfonamide and the method of its preparation. Method of preparation 2-Nitrochlorobenzene-4- (N, 4-carboxyphenyl) - sulfonamide of formula I Cl LO. no2 (AND) so2-nh the water-soluble salt of the acid 4-aminobenzoic acid is reacted in aqueous medium and 2-nitrochlorobenzene-2-sulfonyl chloride at pH 2 to 9, preferably pH 5 to 7. A preferred pH range within a specified range maintains the pH control meter during synthesis with sodium hydroxide feed blocking or with works in a suitable buffer environment - e.g. bicarbonate.
Description
(57) Řešeni spadá do oblasti chemie organických barviv a pigmentů a přípravků pro protimolovou ochranu. Cílem řešení je sloučenina 2-nitrochlorbenzen-4-(N,4’-karboxyfenyl)sulfonamid a způsob její přípravy. Způsob přípravy 2-nitrochlorbenzen-4-(N, 4 1-karboxyfenyl)sulfonamidu vzorce I(57) The solution falls within the field of chemistry of organic dyes and pigments and antimoll protection products. The object of the present invention is the compound 2-nitrochlorobenzene-4- (N, 4'-carboxyphenyl) sulfonamide and a process for its preparation. Preparation of 2-nitrochlorobenzene-4- (N, 1 4 -karboxyfenyl) sulfonamide of formula I
ClCl
LO.LO.
no2 (I) so2-nhno 2 (I) with 2- nm
spočívá v tom, že se vodorozpustná sůl kyseliny 4-aminobenzoové nechá reagovat ve vodném prostředí a 2-nitrochlorbenzen-2-sulfonylchloridem při pH 2 až 9, s výhodou pH 5 až 7. Oblast výhodného pH se ve stanoveném rozmezí udržuje při syntéze regulačním pH-metrem s blokací nátoku hydroxidu sodného nebo se pracuje v prostředí vhodného pufru - např. hydrogenuhličitanu.consists in reacting the water-soluble salt of 4-aminobenzoic acid in an aqueous medium and with 2-nitrochlorobenzene-2-sulfonyl chloride at a pH of 2 to 9, preferably a pH of 5 to 7. The preferred pH range is maintained within a certain range -meter to block the influx of sodium hydroxide or working in a suitable buffer - such as bicarbonate.
CS 265 433 BlCS 265 433 Bl
Vynález se týká 2-nitrochlorbenzen-4-(N,41-karboxyfenyl)sulfonamidu a způsobu jeho výroby.The invention relates to 2-nitrochlorobenzene-4- (N, 4 -karboxyfenyl 1) sulphonamide and its production method.
Byla připravena sloučenina 2-nitrochlorbenzen-4-(N,41-karboxyfenyl)sulfonamid, která může sloužit k dalším syntézám v oblasti chemie organických barviv a pigmentů nebo v oblasti přípravy protimolových prostředků.Compound was prepared 2-nitrochlorobenzene-4- (N, 4 -karboxyfenyl 1) sulfonamide which may be used for further syntheses in chemistry of organic dyes and pigments or in the preparation of moth means.
Způsob přípravy 2-nitrochlorbenzen-4-(N,4'-karboxyfenyl)sulfonamidu vzorce XA process for the preparation of 2-nitrochlorobenzene-4- (N, 4'-carboxyphenyl) sulfonamide of formula X
ClCl
spočívá v tom, že se vodorozpustná sůl kyseliny 4-aminobenzoové nechá reagovat s 2-nitrochlorbenzen-4-sulfonylchloridem ve vodném prostředí při pH 2 až 9, s výhodou pH 5 až 7.characterized in that the water-soluble salt of 4-aminobenzoic acid is reacted with 2-nitrochlorobenzene-4-sulfonyl chloride in an aqueous medium at a pH of 2 to 9, preferably a pH of 5 to 7.
Při vlastni syntéze se oblast výhodného pH udržuje ve stanoveném rozmezí prostřednictvím automatického regulačního pH-metru s blokací nátoku hydroxidu sodného nebo se pracuje v prostředí vhodného pufru - např. hydrogenuhličitanu.In the actual synthesis, the preferred pH range is maintained within a specified range by means of an automatic pH-regulating meter with blocking of sodium hydroxide influx or working in a suitable buffer - e.g., bicarbonate.
Provedení podle vynálezu upřesňují uvedené příklady.Embodiments of the invention are illustrated by the examples.
Příklad 1Example 1
13,9 g 100% kyseliny 4-aminobenzoové se suspenduje ve 100 ml vody a rozpustí přídavkem roztoku hydroxidu sodného na pH 7,5. Rovnoměrně rychle se za účinného míchání a při teplotě 20 až 50 °C do vzniklého roztoku nadávkuje 25,6 g 100% 2-nitrochlorbenzen-4-sulfonylchloridu (0,1 mol) a vznikající kyselost se otupuje roztokem hydroxidu sodného o koncentraci c(NaOH) = = 10 mol/1 tak, aby vznikal roztok s pH 5 až 7, a to průběžně.13.9 g of 100% 4-aminobenzoic acid are suspended in 100 ml of water and dissolved to pH 7.5 by addition of sodium hydroxide solution. 25.6 g of 100% 2-nitrochlorobenzene-4-sulfonyl chloride (0.1 mol) was metered into the resulting solution evenly with efficient stirring at 20 to 50 ° C, and the resulting acid was blunted with sodium hydroxide solution c (NaOH) ) = 10 mol / l to form a solution with a pH of 5 to 7 continuously.
Po několikahodinovém doreagování se reakční směs vyhřeje na 50 až 60 °C a za míchání se vykyselí kyselinou chlorovodíkovou o koncentraci c(HCl) = 9 mol/1 na pH 1.After several hours of reaction, the reaction mixture is heated to 50-60 ° C and acidified with stirring to a pH of 1 with c (HCl) = 9 mol / l hydrochloric acid.
Suspenze látky vzorce I se odfiltruje a filtrační koláč se promyje teplou vodou do ztráty kyselé reakce filtrátů. Získá se 29,2 g 100% látky vzorce I o t.t. 282 až 285 °C.The suspension of the compound of formula I is filtered off and the filter cake is washed with warm water until the acidic reaction of the filtrates is lost. 29.2 g of 100% of the compound of formula I of m.p. Mp 282-285 ° C.
Přiklad 2Example 2
13,9 g 100% kyseliny 4-aminobenzoové se suspenduje ve 100 ml vody a rozpustí přídavkem 12,5 g hydrogenuhličitanu sodného. Rovnoměrně rychle se za účinného míchání a při teplotě 20 až 50 °C a pH 8 začne dávkovat 25,6 g 100% 2-nitrochlorbenzen-4-sulfonylohloridu (0,1 mol). Během dávkování a reakce se udržuje hladina pH na 5 až 7. Vlastní rychlost dávkováni sulfonylchloridu musí být řízena i s ohledem na intenzitu pěnění reakční směsi.13.9 g of 100% 4-aminobenzoic acid are suspended in 100 ml of water and dissolved by the addition of 12.5 g of sodium bicarbonate. 25.6 g of 100% 2-nitrochlorobenzene-4-sulfonyl chloride (0.1 mol) are metered in evenly quickly with efficient stirring and at a temperature of 20 to 50 ° C and pH 8. The pH level is maintained at 5 to 7 during dosing and reaction. The actual rate of sulfonyl chloride dosing must also be controlled with respect to the foaming intensity of the reaction mixture.
Po několikahodinovém doreagování se reakční směs vyhřeje na teplotu 50 až 60 °C a za míchání se vykyselí kyselinou chlorovodíkovou na pH 1.After several hours of reaction, the reaction mixture was heated to 50-60 ° C and acidified to pH 1 with hydrochloric acid with stirring.
Pevný podíl látky vzorce I se odfiltruje a filtrační koláč se promyje teplou vodou do ztráty kyselé reakce filtrátů, získá se 29,2 g 100% látky vzorce I s výše uvedenou t.t.The solid of Formula I is filtered off and the filter cake is washed with warm water until the acidic reaction of the filtrates is lost, yielding 29.2 g of 100% of Formula I with the above m.p.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881302A CS265433B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrochlorbenzen-4-/n,4-carboxyphenyl/sulphamide and process for preparing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881302A CS265433B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrochlorbenzen-4-/n,4-carboxyphenyl/sulphamide and process for preparing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS130288A1 CS130288A1 (en) | 1989-01-12 |
| CS265433B1 true CS265433B1 (en) | 1989-10-13 |
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ID=5347060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS881302A CS265433B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrochlorbenzen-4-/n,4-carboxyphenyl/sulphamide and process for preparing them |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS265433B1 (en) |
-
1988
- 1988-03-01 CS CS881302A patent/CS265433B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS130288A1 (en) | 1989-01-12 |
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