CS265725B1 - 2-nitrochlorbenzen-4-/n,2-karboxyphenyl/sulphonamide and process for preparing thereof - Google Patents
2-nitrochlorbenzen-4-/n,2-karboxyphenyl/sulphonamide and process for preparing thereof Download PDFInfo
- Publication number
- CS265725B1 CS265725B1 CS881311A CS131188A CS265725B1 CS 265725 B1 CS265725 B1 CS 265725B1 CS 881311 A CS881311 A CS 881311A CS 131188 A CS131188 A CS 131188A CS 265725 B1 CS265725 B1 CS 265725B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- nitrochlorobenzene
- anthranilic acid
- sulfonyl chloride
- formula
- carboxyphenyl
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 7
- 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
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims abstract description 28
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003456 sulfonamides Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 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 abstract description 3
- 239000000975 dye Substances 0.000 abstract description 3
- -1 2-carboxyphenyl Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 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
- 125000003368 amide group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- STJUJXONQFLCOP-UHFFFAOYSA-L lithium;sodium;carbonate Chemical compound [Li+].[Na+].[O-]C([O-])=O STJUJXONQFLCOP-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Řešeni spadá do oblasti chemie organických barviv a přípravků pro protimolovou ochranu. Cílem řešení je sloučenina 2-nitrochlorbenzen-4-{l, 2 '-karboxyfenyl)- sulfonamid a způsob její přípravy._Způsob přípravy 2-nitrochlorbenzen-4-(N,2 -karboxyfenyl)sulfonamidu vzorce I spočívá v tom, že se vočtorozpustná sůl kyseliny antranilové nechá reagovat v množství 1 až 1,4 molu s 2-nitrochlorbenzen-4-sulfonylchloridem, s výhodou 1,3 molu kyseliny antranilové na 3 mol sulfonylchloridu, při pH 2 až 9 s výhodou pil 5 až 7The solution falls within the field of chemistry organic dyes and antimol protection. The goal of the solution is the compound 2-Nitrochlorobenzene-4- (1,2'-carboxyphenyl) - a sulfonamide and a process for its preparation to prepare 2-nitrochlorobenzene-4- (N, 2-carboxyphenyl) sulfonamide formula I is based on the insoluble salt of anthranilic acid 1 to 1.4 moles with 2-nitrochlorobenzene-4-sulfonyl chloride, preferably 1.3 mol of anthranilic acid to 3 moles of sulfonyl chloride, at pH 2 to 9 preferably saws 5 to 7
Description
Vynález se týká 2-nitrochlorbenzen-4-(N,2'-karboxyfenyl)sulfonamidu a způsobu jeho výroby.The present invention relates to 2-nitrochlorobenzene-4- (N, 2'-carboxyphenyl) sulfonamide and to a process for its preparation.
Byla připravena sloučenina 2-nítroch]orbenzen-4-(N,2'-karboxyfenyl)sulfonaroid, která může sloužit k dalším syntézám, v oblasti' chemie organických barviv nebo v oblasti přípravy 111 ι»I i nt«»11 >v ý< ·Ιι | ί i ml Γ IV. ΰ .The compound 2-nitro] orbenzene-4- (N, 2'-carboxyphenyl) sulfonaroid has been prepared, which can be used for further syntheses, in the field of organic dye chemistry or in the field of preparation of dyes. <· Ιι | i i ml Γ IV. ΰ.
Způsob př ípravy 2-nitrochlorbcnzen-4- (N, 2 '-karboxy feny 1) sulfonamidu vzorce IProcess for the preparation of 2-nitrochlorobenzene-4- (N, 2'-carboxyphenyl) sulfonamide of formula I
Cl (I) spočívá v tom, že se vodorozpustná sůl kyseliny antranilové nechá reagovat v množství 1 až 1,4 molu s 2-n.ítrochlo.rbenzen-4-sulfonylchloridem, s výhodou 1,3 molu kyseliny antranilové na 1 mol sulfony1 chloridu, při pH 2 až 9 s výhodou pH 5 az 7.Cl (I) is characterized in that the water-soluble anthranilic acid salt is reacted in an amount of 1 to 1.4 moles with 2-nitroblo-benzene-4-sulfonyl chloride, preferably 1.3 moles of anthranilic acid per 1 mol of sulfonyl chloride , at a pH of 2 to 9, preferably a pH of 5 to 7.
Při vlastní syntéze se oblast výhodného pH udržuje ve stanoveném rozmezí prostřednictvím automatického regulačního píl-metru s blokací nátoku hydroxidu sodného nebo se pracuje v prostředí vhodného pufru - např. kyselého uhličitanu sodného.In the actual synthesis, the preferred pH range is maintained within a specified range by means of an automatic control pill meter with sodium hydroxide influx blocking or working in a suitable buffer - e.g. sodium bicarbonate.
Na výtěžnost syntézy má vliv molární poměr mezi reagujícími komponentami. Při ekvimolárním poměru kys. antranilové a 2-nitrochlorbenzen-4-sulfonylchloridem se dosahuje výtěžnosti 85 % teorie (počítáno na sulfonylchlorid). Pokud se molární poměr zvýší na hodnotu 1,3 molu kys. antranilové na 1 mol sulfonylchloridu, zvýší se výtěžnost syntézy na 92 % teorie na sulfonylchlorid. Kyselinu antranilovou lze potom vyloučit z matečných louhů po izolaci látky vzorce I vykyselením na pfí 3,8 až 4,2 a následnou filtrací. Takto získaná kyselina antranilová se vrací zpět do syntézy. Tímto způsobem se dosáhne vyššího využití primárních surovin a zlepší se ekologie odpadních vod.The mole ratio between the reacting components influences the yield of the synthesis. With an equimolar ratio of anthranilic acid and 2-nitrochlorobenzene-4-sulfonyl chloride, a yield of 85% of theory (calculated on sulfonyl chloride) is achieved. If the molar ratio is increased to 1.3 moles of anthranilic acid per mole of sulfonyl chloride, the synthesis yield will increase to 92% of theory to the sulfonyl chloride. The anthranilic acid can then be separated from the mother liquors after isolation of the compound of formula I by acidification to pH 3.8 to 4.2 and subsequent filtration. The anthranilic acid thus obtained is returned to the synthesis. In this way, the use of primary raw materials is increased and the waste water ecology is improved.
Získaná látka vzorce I má stanovenu teplotu tání 203 až 206 °C, její titraci hydroxidem sodným ve vodném prostředí do 1 až 2 stupně s užitím potenciometrické indikace byla potvrzena přítomnost karboxylové a amidické skupiny a z obou stupňů vypočtena relativní molární hmotnost 356,5.The compound of formula (I) obtained has a melting point of 203 DEG-206 DEG C., its titration with sodium hydroxide in aqueous medium to 1 to 2 degrees using a potentiometric indication, confirms the presence of the carboxyl and amide groups, and calculates a relative molar mass of 356.5.
Provedení podle vynálezu upřesňují uvedené příklady.Embodiments of the invention are illustrated by the examples.
Příklad 1Example 1
13,9 g 100% kyseliny antranilové 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) vznikající kyselost se otupuje roztokem hydroxidu sodného o koncentraci c(NaOH) = = 10 mol/1 tak, aby průběžně vznikal roztok s pH 5 až 7.13.9 g of 100% anthranilic 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) were added to the resulting solution uniformly rapidly with efficient stirring at 20 to 50 ° C, and the resulting acidity was blunted with sodium hydroxide solution c (NaOH). = 10 mol / l so that a solution with a pH of 5-7 is continuously formed.
Po několika hodinovém doreagováni se reakční směs vyhřeje na 50 až 60 °C za míchání se vykyselí kyselinou chlorovodíkovou o koncentraci c/HCl) = 9 mol/1 na pH 1.After a few hours of reaction, the reaction mixture was heated to 50-60 ° C and acidified to pH 1 with hydrochloric acid (c / HCl) = 9 mol / L with stirring.
Pevný podíl látky vzorce I se odfiltruje a filtračni koláč se promyje teplou vodou do ztráty kyselé reakce filtrátů. Získá se 30,3 g 100% látky vzorce I o teplotě tání 203 až 206 °C.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. 30.3 g of 100% of the compound of formula I are obtained, m.p. 203 DEG-206 DEG.
Příklad 2 .13,9 g 100% kyseliny antranilové se suspenduje ve 100 ml vody a rozpustí přídavkem 12,5 g liydí ogcnuhl ič ί I .'mu sodného. Rovnou/’ rnř rychle se zn účinného míchání a při teplot/· až. 50 °C a pH 8 začne dávkovat 25,6 g 100% 2-nitrochlorbenzen-4-sulíoriylchloridu (o. I mel i . Hěli.m <1<U en.píván ( ne pil reakce udržuje na úrovni pil 5 až 7 1 případným přídavkem liydr ogcnuhl i č i l amí. Rychlost dávkování nu 1 tony leh Joridu umní být. řízena i n ohledem na intenzitu pěnění reakční směsi.EXAMPLE 2 13.9 g of 100% anthranilic acid are suspended in 100 ml of water and dissolved by the addition of 12.5 g of sodium lithium carbonate. Directly mix effectively and at temperatures up to. 50 ° C and pH 8 starts to dispense 25.6 g of 100% 2-nitrochlorobenzene-4-sulforiyl chloride (o.I mel i. Heli.m <1 <U env. The feed rate of 1 tonne of chloride can be controlled with respect to the foaming intensity of the reaction mixture.
Po několika hodinovém doreagování se reakční směs vyhřeje na teplotu 50 až 60 °C a za míchání se vykyselí kyselinou chlorovodíkovou na ptl 1.After a few hours of reaction, the reaction mixture was heated to 50-60 ° C and acidified to pH 11 with hydrochloric acid with stirring.
Pevný podíl látky vzorce I se odfiltruje a filtrační koláč se promyje. teplou vodou do z.tráty kyselé reakce filtrátů. Výtěžek činí 30,4 g látky (100%) vzorce 1.The solid of formula I is filtered off and the filter cake is washed. warm water to the loss of acidic reaction of the filtrates. Yield: 30.4 g (100%) of Formula 1.
Příklad 3Example 3
18,1 g 100% kyseliny antranilové (1,3 mol) se suspenduje ve 'vodě (100 ml) a rozpustí se přídavkem hydroxidu sodného na pil 7,5. Rovnoměrně rychle se za míchání a při teplotě 20 až 50 °C dávkuje do roztoku 25,6 g 100% 2-rii.trochlorbenzen-4-sulfonylchloridu (0,1 mol). Během doreagování se udržuje pH 5 až 7 otupováním hydroxidem sodným.18.1 g of 100% anthranilic acid (1.3 mol) was suspended in water (100 ml) and dissolved by addition of sodium hydroxide to pH 7.5. 25.6 g of 100% 2-trifluorobenzene-4-sulfonyl chloride (0.1 mol) was added to the solution with uniform stirring at 20-50 ° C. During the post-reaction, the pH is maintained at 5-7 by blinding with sodium hydroxide.
Po doreagování se reakční směs vyhřeje na teplotu 50 až 60 °C a za míchání se vykyselí kyselinou chlorovodíkovou na pH 1.After reaction, the reaction mixture was heated to 50-60 ° C and acidified with hydrochloric acid to pH 1 with stirring.
Pevný podíl látky vzorce I se odfiltruje a filtrační koláč se promyje teplou vodou do neutrální reakce filtrátů.The solid of formula I is filtered off and the filter cake is washed with warm water until the filtrate is neutral.
Zachycené filtráty se vykyselí kyselinou chlorovodíkovou na pH 4, suspenze kys. antranilové se zfiltruje a filtrační koláč se promyje vodou do neutrální reakce filtrátů.The collected filtrates were acidified to pH 4 with hydrochloric acid, the anthranilic acid suspension was filtered, and the filter cake was washed with water until the filtrate was neutralized.
Získaná kyselina antranilové Se vrací zpět do reakce. Získá se 32,6 g 100% látky vzorce 1.The obtained anthranilic acid is returned to the reaction. 32.6 g of 100% of the compound of formula 1 are obtained.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881311A CS265725B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrochlorbenzen-4-/n,2-karboxyphenyl/sulphonamide and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS881311A CS265725B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrochlorbenzen-4-/n,2-karboxyphenyl/sulphonamide and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS131188A1 CS131188A1 (en) | 1989-02-10 |
| CS265725B1 true CS265725B1 (en) | 1989-11-14 |
Family
ID=5347178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS881311A CS265725B1 (en) | 1988-03-01 | 1988-03-01 | 2-nitrochlorbenzen-4-/n,2-karboxyphenyl/sulphonamide and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS265725B1 (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 CS881311A patent/CS265725B1/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 |
|---|---|
| CS131188A1 (en) | 1989-02-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR950014212B1 (en) | Aluminium ploychlorosulphates, process for their preparation and their used | |
| CS265725B1 (en) | 2-nitrochlorbenzen-4-/n,2-karboxyphenyl/sulphonamide and process for preparing thereof | |
| SU719496A3 (en) | Method of preparing arylenebissulfonyl ureas | |
| GB2075968A (en) | Benzylsulphonic acid derivatives | |
| DE68911540T2 (en) | PRODUCTION OF 2- (CHLORO, BROMO OR NITRO) -4- (ALKYLSULFONYL) -BENZOIC ACID AND INTERMEDIATE PRODUCTS. | |
| RU2147576C1 (en) | Method of synthesis of dimethyldithiocarbamate sodium | |
| CS265432B1 (en) | 2-nitrochlorbenzen-4-/n,3-carboxyphenyl/sulphonamide and process for preparing thereof | |
| CS264929B1 (en) | 2-nitrophenyl-4-/n-carboxyphenyl-sulphonamid and process for preparing thereof | |
| US4257977A (en) | 2-Nitro-4'-aminodiphenylamine-2',4-disulfonic acid and process for its preparation | |
| EP0010443B1 (en) | Process for preparing sodium-m-nitrobenzenesulfonate | |
| US5315036A (en) | Process for the preparation of 2-aminobenzene-1,4-disulphonic acids and the new compound 6-chloro-2-aminobenzene-1,4-disulphonic acid | |
| JPS6127980A (en) | Preparation of hydroxyflavan compound | |
| JP2987058B2 (en) | Method for producing sodium 3-alizarin sulfonate | |
| SU453838A3 (en) | METHOD OF OBTAINING DOUBLE BENCH HETEROCYCLIC ALCOHOLS | |
| CS265433B1 (en) | 2-nitrochlorbenzen-4-/n,4-carboxyphenyl/sulphamide and process for preparing them | |
| DE3501754A1 (en) | Sulphonation of ortho-nitrochlorobenzene, para-nitrochlorobenzene and ortho-nitrotoluene | |
| SU1097623A1 (en) | Process for preparing dipotassium salt of 4,5-dihydroxyimidazolidinedisulfonic acid-1,3 | |
| SU1159920A1 (en) | Method of obtaining 2-(2'-oxy-5'-methylphenyl)-0-benztriazole | |
| Rowe et al. | 93. A reaction of certain diazosulphonates derived from β-naphthol-1-sulphonic acid. Part XX. The stabilities of acrylic acid derivatives from sodium 1-arylazo-β-naphthaquinone-1-sulphonate and its derivatives, and an investigation of derived iso indolinones | |
| EP0038999B1 (en) | Process for preparing 2-chloro-5-formyl benzene sulphonic acid | |
| JPS6127979A (en) | Preparation of hydroxyflavan compound | |
| DE2346308A1 (en) | Isatoic anhydride prepn. - by oxidation of phthalamate salts with hypohalites in the presence of halogen or haloamide and a polymerisation inhibitor | |
| JPS5910656B2 (en) | Method for producing 1-amino-naphthalene-7-sulfonic acid | |
| CS264796B1 (en) | 2-nitrophenol-4-n,4 -carboxyphenyl/sulphonamide and process for preparing them | |
| CS247046B1 (en) | Preparation method of 4-fluorine-2-(4-isopropylphenylthio)benzoic acid |