DE2639668A1 - 2-acylamino-5-chlor-benzolsulfonsaeuren - Google Patents
2-acylamino-5-chlor-benzolsulfonsaeurenInfo
- Publication number
- DE2639668A1 DE2639668A1 DE19762639668 DE2639668A DE2639668A1 DE 2639668 A1 DE2639668 A1 DE 2639668A1 DE 19762639668 DE19762639668 DE 19762639668 DE 2639668 A DE2639668 A DE 2639668A DE 2639668 A1 DE2639668 A1 DE 2639668A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compounds
- acid
- carboxy group
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- WVYIZGMCLSGZGG-UHFFFAOYSA-N 10-hydroxy-cis-12-octadecenoic acid Natural products CCCCCC=CCC(O)CCCCCCCCC(O)=O WVYIZGMCLSGZGG-UHFFFAOYSA-N 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 Isopropyl compound Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 3
- VEPOZWJTGLVFEU-UHFFFAOYSA-N 5-acetamido-2-chloro-4-sulfobenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=C(Cl)C=C1S(O)(=O)=O VEPOZWJTGLVFEU-UHFFFAOYSA-N 0.000 description 3
- JGSAMPZLJLDOKW-UHFFFAOYSA-N 5-amino-2-chloro-4-sulfobenzoic acid Chemical compound NC1=CC(C(O)=O)=C(Cl)C=C1S(O)(=O)=O JGSAMPZLJLDOKW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 229960001841 potassium permanganate Drugs 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- UPMIEBBZKWZYEZ-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1Cl UPMIEBBZKWZYEZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- UYEKNNXCZHSNCX-UHFFFAOYSA-N (5-amino-2-chlorophenyl)methanesulfonic acid Chemical compound NC1=CC=C(Cl)C(CS(O)(=O)=O)=C1 UYEKNNXCZHSNCX-UHFFFAOYSA-N 0.000 description 1
- VBNFOVAJFHWUAN-UHFFFAOYSA-N 2-acetamido-4-(2-chloroethyl)benzenesulfonic acid Chemical compound ClCCC1=CC=C(C(=C1)NC(C)=O)S(=O)(=O)O VBNFOVAJFHWUAN-UHFFFAOYSA-N 0.000 description 1
- VIYONYBARUSSCC-UHFFFAOYSA-N 2-amino-4-(2-chloroethyl)benzenesulfonic acid Chemical compound NC1=CC(CCCl)=CC=C1S(O)(=O)=O VIYONYBARUSSCC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000242711 Fasciola hepatica Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000816 effect on animals Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 208000006275 fascioliasis Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762639668 DE2639668A1 (de) | 1976-09-03 | 1976-09-03 | 2-acylamino-5-chlor-benzolsulfonsaeuren |
| CH1062377A CH632242A5 (en) | 1976-09-03 | 1977-08-31 | Process for preparing 2-acylamino-5-chlorobenzenesulphonic acids |
| IT2719177A IT1085035B (it) | 1976-09-03 | 1977-09-01 | Acidi 2-acilamino-5-cloro-benzensolfonici |
| JP10504977A JPS5331644A (en) | 1976-09-03 | 1977-09-02 | 22acylaminoo55chloroobenzolsufonic acid |
| GB3674377A GB1584823A (en) | 1976-09-03 | 1977-09-02 | 2-acylamino-5-chlorobenzenesulphonic acids useful as intermediates in the production of diazo components |
| FR7726813A FR2363548A1 (fr) | 1976-09-03 | 1977-09-05 | Acides acylamino-2 chloro-5 benzene-sulfoniques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762639668 DE2639668A1 (de) | 1976-09-03 | 1976-09-03 | 2-acylamino-5-chlor-benzolsulfonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2639668A1 true DE2639668A1 (de) | 1978-03-09 |
Family
ID=5987047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762639668 Withdrawn DE2639668A1 (de) | 1976-09-03 | 1976-09-03 | 2-acylamino-5-chlor-benzolsulfonsaeuren |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5331644A (enrdf_load_stackoverflow) |
| CH (1) | CH632242A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2639668A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2363548A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1584823A (enrdf_load_stackoverflow) |
| IT (1) | IT1085035B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1436059A (en) * | 1974-04-18 | 1976-05-19 | Ici Ltd | 2-amino-4,5-disulphobenzoic acid and derivatives |
-
1976
- 1976-09-03 DE DE19762639668 patent/DE2639668A1/de not_active Withdrawn
-
1977
- 1977-08-31 CH CH1062377A patent/CH632242A5/de not_active IP Right Cessation
- 1977-09-01 IT IT2719177A patent/IT1085035B/it active
- 1977-09-02 GB GB3674377A patent/GB1584823A/en not_active Expired
- 1977-09-02 JP JP10504977A patent/JPS5331644A/ja active Pending
- 1977-09-05 FR FR7726813A patent/FR2363548A1/fr active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1085035B (it) | 1985-05-28 |
| GB1584823A (en) | 1981-02-18 |
| JPS5331644A (en) | 1978-03-25 |
| FR2363548B1 (enrdf_load_stackoverflow) | 1981-06-12 |
| CH632242A5 (en) | 1982-09-30 |
| FR2363548A1 (fr) | 1978-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69208120T2 (de) | Verfahren zur Herstellung von Ferulasäure | |
| EP0039482A2 (de) | Perylen-3,4,9,10-tetracarbonsäuremonoanhydridmonoimide, Verfahren zur Herstellung solcher Verbindungen und ihre Verwendung | |
| DE1445506C3 (de) | Verfahren zur Gewinnung von reinem a-Aminobenzylpenicillin | |
| DE2156662C3 (de) | Verfahren zur Herstellung von 3,3-Bis(4-dimethylaminophenyl)-6-dimethylaminophthalid (Kristallviolettalacton) | |
| EP0045375A1 (de) | Verfahren zur Herstellung von Chinolinen, Naphthyridinen und anderen Stickstoff-bi-heterocyclen | |
| DE2051269B2 (de) | Verfahren zur Herstellung von 3-Propiony !salicylsäure | |
| CH635065A5 (de) | Verfahren zum trennen von gemischen aus 3- und 4-nitrophthalsaeure. | |
| DE2639668A1 (de) | 2-acylamino-5-chlor-benzolsulfonsaeuren | |
| EP0011207B1 (de) | Verfahren zur Herstellung von 3,3-Dimethyl-2-oxobuttersäure | |
| EP0417543B1 (de) | Verfahren zur Herstellung von 3-Methylchinolin-8-carbonsäure | |
| DE913177C (de) | Verfahren zur Herstellung heterocyclischer AEthersulfone | |
| DE880137C (de) | Verfahren zur Herstellung von Bleiphthalaten | |
| DE2215048B2 (de) | Verfahren zur Herstellung von 2- [Bis-(4,4'dialkylamino)-benzhydryl] -5- aminobenzoesäuren | |
| DE2061430B2 (de) | Verfahren zur Herstellung von 4-Mercaptopyrazolo eckige Klammer auf 3,4d eckige Klammer zu pyrimidinen | |
| DE1643499C3 (de) | Verfahren zur Reduktion von Nitrobenzoldicarbonsäure-(3,4) | |
| DE951006C (de) | Verfahren zur Herstellung von substituierten Oxazol-5-on-verbindungen | |
| DE1620459C3 (de) | Verfahren zur Herstellung von 2H-1,2,4-Benzothiadiazin-1,1 -dioxidderi vaten | |
| DE924212C (de) | Verfahren zur Herstellung von ringsubstituierten ª -Oxybrenztrauben-saeuren bzw. deren Derivaten | |
| EP0057665B1 (de) | Verfahren zur Herstellung von 1-Acylamino-3,4-phthaloyl-acridonen | |
| DE247411C (enrdf_load_stackoverflow) | ||
| DE1695012C3 (de) | N hoch 1 -(6-Cyclopropyl-4-pyrimidinyl)-sulfanilamide | |
| DE2166456C3 (de) | Verfahren zur Herstellung von N-Diäthylaminoäthyl-2-methoxy-4-amino-5-chlorbenzamid | |
| DE1468723A1 (de) | Verfahren zur Reinigung von Terephthalsaeure | |
| DE1695898C3 (de) | Verfahren zur Herstellung von Riboflavintetrabutyrat | |
| DE1543521C (de) | Verfahren zur Herstellung von jodiertem Lecithin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| 8136 | Disposal/non-payment of the fee for publication/grant |