GB533495A - Manufacture of new benzenesulphonamido-derivatives - Google Patents
Manufacture of new benzenesulphonamido-derivativesInfo
- Publication number
- GB533495A GB533495A GB3109/39A GB310939A GB533495A GB 533495 A GB533495 A GB 533495A GB 3109/39 A GB3109/39 A GB 3109/39A GB 310939 A GB310939 A GB 310939A GB 533495 A GB533495 A GB 533495A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- group
- thiazole
- prepared
- aminobenzenesulphonamido
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
533,495. Sulphonamide compounds. SOC. OF CHEMICAL INDUSTRY IN BASLE. Jan. 30, 1939, Nos. 3109, 3110, 3111 and 3112. Convention dates, Jan. 31, 1938, Sept. 16; 1938, Nov. 24, 1938 and Dec. 22, 1938. [Class 2 (iii)] Benzene-sulphonamide-thiazole compounds containing in the p-position an amino group or a substituent convertible into an amino group are prepared by the methods known for the production of the corresponding compounds in which the thiazole residue is replaced by a hydrocarbon radicle. The convertible substituents consist of an acylamino, nitro, nitroso, azo or hydrazo group or a halogen atom. Thus, a benzene-sulphonic acid halide or ester, appropriately substituted, may be reacted with an aminothiazole; or the corresponding benzene-sulphonamide may be treated with a halogenthiazole. When the p-substituent is one convertible into an amino group it may be so converted ; if an amino group is present, it may be substituted and comprise, for example, an alkylamino, N-acyl-N-alkylamino or aralkylamino group. The benzene-sulphonic acid derivative may contain other substituents such as an alkyl group, whilst the amino thiazoles may be replaced by aminoalkylthiazoles. The products possess therapeutic properties. According to the example, 2-(p-aminobenzenesulphonamido)-thiazole is prepared by (1) heating acetylsulphanilic acid chloride, made from acetanilide and chlorosulphonic acid, with 2-aminothiazole in aqueous solution and treating the resulting (bis-p-acetaminobenzenesulpho)-2-aminothiazole with caustic soda solution ; (2) heating p-acetaminobenzene-sulphonamide with 2-bromthiazole in the presence of potassium carbonate and copper powder, and hydrolyzing the resulting 2-(p-acetaminobenzenesulphonamido)-thiazole. In a manner analogous to (1) is prepared 2-(p-aminobenzenesulphonamido) - 4 - methylthiazole via (bis - p - acetaminobenzenesulpho) - 2 - amino - 4 - methylthiazole. The Specification as open to inspection under Sect. 91 also describes the preparation of compounds containing any heterocyclic nucleus in place of the thiazole residue, by the use of the amino- or halogen-substituted heterocyclic compounds. Of the latter are specified 1-, 2- and 3-aminopyridines, alkylaminopyridines, arylaminopyridines, arylalkylaminopyridines, diaminopyridines, nitroaminopyridines, aminopyridinecarboxylic acids, aminoquinolines, amino-isoquinolines, aminoacridines, amino-oxazoles, halogenpyridines such as 1-bromo-, 3-chloro- and 3 : 5-dibromopyridines, and 2-bromquinoline. It also includes two examples, according to which (1) acetylsulphanilic acid chloride is reacted in cold aqueous potassium hydroxide solution with 2-aminopyridine and the resulting 2- (p - acetaminobenzenesulphonamido) - pyridine then hydrolyzed with caustic soda to split off the acetyl group ; in like manner are prepared 2 - (p - aminobenzenesulphonamido) - 6 - aminopyridine its acetyl derivative, and 2-[p-(p<SP>1</SP>- benzenesulphonamido) - benzenesulphonamido]- pyridine ; (2) acetylsulphanilic acid chloride is stirred into a cold aqueous solution of 3- aminopyridine and the resulting 3-(p-acetaminobenzenesulphonamido) - pyridine hydrolyzed with caustic soda ; 4-(p-aminobenzenesulphonamido)-pyridine and its acetyl derivative are similarly prepared. This subjectmatter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH533495X | 1938-01-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB533495A true GB533495A (en) | 1941-02-14 |
Family
ID=4518616
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3109/39A Expired GB533495A (en) | 1938-01-31 | 1939-01-30 | Manufacture of new benzenesulphonamido-derivatives |
Country Status (2)
Country | Link |
---|---|
CY (1) | CY66A (en) |
GB (1) | GB533495A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2482085A (en) * | 1944-06-23 | 1949-09-20 | Monsanto Chemicals | Method for the preparation of sulfathiazoles |
US2921066A (en) * | 1957-04-18 | 1960-01-12 | Bayer Ag | Sulfonamides |
US3467653A (en) * | 1965-10-15 | 1969-09-16 | Merck & Co Inc | Anticoccidial sulfanilamidothiadiazoles |
-
1939
- 1939-01-30 GB GB3109/39A patent/GB533495A/en not_active Expired
-
1947
- 1947-05-17 CY CY6647A patent/CY66A/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2482085A (en) * | 1944-06-23 | 1949-09-20 | Monsanto Chemicals | Method for the preparation of sulfathiazoles |
US2921066A (en) * | 1957-04-18 | 1960-01-12 | Bayer Ag | Sulfonamides |
US3467653A (en) * | 1965-10-15 | 1969-09-16 | Merck & Co Inc | Anticoccidial sulfanilamidothiadiazoles |
Also Published As
Publication number | Publication date |
---|---|
CY66A (en) | 1947-05-17 |
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