GB795937A - Benzoic acid-4-sulphonamides - Google Patents
Benzoic acid-4-sulphonamidesInfo
- Publication number
- GB795937A GB795937A GB34188/55A GB3418855A GB795937A GB 795937 A GB795937 A GB 795937A GB 34188/55 A GB34188/55 A GB 34188/55A GB 3418855 A GB3418855 A GB 3418855A GB 795937 A GB795937 A GB 795937A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- group
- propylamide
- sulphonic
- sulphochloride
- 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.)
- Expired
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 7
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 abstract 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 abstract 2
- -1 ethyl-butamine Chemical compound 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 abstract 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 150000003974 aralkylamines Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000005521 carbonamide group Chemical group 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- 229940045803 cuprous chloride Drugs 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 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
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (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)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the production of benzoic acid-4-sulphonamides comprises reacting a benzoic acid-4-sulphohalide substituted in the 2-position of the phenyl radical by a methyl group, a chlorine atom or a group which can be replaced by a chlorine atom, with a mono- or di-alkylamine, piperidine or a C-alkyl piperidine or an aralkylamine, said amine having a total of not less than 5 and not more than 8 carbon atoms and, in the case where the substituent in the 2-position of the phenyl radical is a group which can be replaced by a chlorine atom, replacing said group by a chlorine atom. A modification of the process comprises the use as a starting material of a derivative of a benzoic-acid-4-sulphohalide wherein the carboxy group is replaced by a group convertible thereto, such as cyano, carbonamide and carboxylic acid ester, and this group is converted into the carboxyl group in the sulphonamide which is obtained. The reaction may be carried out in an aqueous or organic solvent medium, preferably in the presence of acid-fixing agents such as alkali metal hydroxides or carbonates or organic bases, e.g. pyridine. Specified amines are di-n-butylamine, di-n-propylamine, di-isopropylamine, ethyl-butamine, piperidine, C-alkyl piperidines, n-hexylamine and benzylamine. In examples: (1) 2 - chlorobenzoic acid - 4 - sulphochloride was reacted with di-n-propylamine, di-n-butylamine, di-isopropylamine, benzylamine and piperidine to give 2-chlorobenzoic acid-4-sulphonic acid-di-n-propylamide, -di-n-butylamide, -di-isopropylamide, -benzylamide and -piperidide; (2) 2-methyl-benzonitrile-4-sulphochloride was reacted with di-n-propylamine to give 2-methyl-benzonitrile-4-sulphonic acid di-n-propylamide which was hydrolysed with alcoholic caustic potash to 2-methyl-benzoic acid-4-sulphonic acid-di-n-propylamide; (3) di-n-propylamine was reacted with 2-nitro-benzoic acid-4-sulphochloride to give 2-nitrobenzoic acid-4-sulphonic acid-di-n-propylamide which was reduced with iron and acetic acid to 2-aminobenzoic acid-4-sulphonic acid-di-n-propylamide which was diazotized and reacted with cuprous chloride and hydrochloric acid to give 2-chlorobenzoic acid-4-sulphonic acid-di-n-propylamide. 2-Chlorobenzoic acid-4-sulphochloride was prepared by treating 2-chlorobenzoic acid-4-sulphonic acid with chlorosulphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE795937X | 1954-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB795937A true GB795937A (en) | 1958-06-04 |
Family
ID=6710851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34188/55A Expired GB795937A (en) | 1954-11-29 | 1955-11-29 | Benzoic acid-4-sulphonamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB795937A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992441A (en) * | 1972-12-26 | 1976-11-16 | Pfizer Inc. | Sulfamylbenzoic acids |
-
1955
- 1955-11-29 GB GB34188/55A patent/GB795937A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992441A (en) * | 1972-12-26 | 1976-11-16 | Pfizer Inc. | Sulfamylbenzoic acids |
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