GB891471A - Benzothiadiazine compounds - Google Patents
Benzothiadiazine compoundsInfo
- Publication number
- GB891471A GB891471A GB21907/58A GB2190758A GB891471A GB 891471 A GB891471 A GB 891471A GB 21907/58 A GB21907/58 A GB 21907/58A GB 2190758 A GB2190758 A GB 2190758A GB 891471 A GB891471 A GB 891471A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aniline
- nitro
- heating
- give
- resulting
- 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
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Abstract
Benzothiadiazine-1 : 1-dioxides of the formula <FORM:0891471/IV (b)/1> or <FORM:0891471/IV (b)/2> wherein R DEG is an amino or nitro group and R1 is hydrogen or a C1-5 alkyl radical are prepared by (a) heating a chloronitroaniline (optionally bearing an alkyl substituent R1 on the amino group), e.g. a 3-chloro-4-nitro-aniline, with an aqueous solution of sodium sulphite, converting the resulting sodium nitroaniline sulphonate to the nitroaniline disulphonyl chloride by reaction with chlorosulphonic acid, reacting with ammonia to give the di-sulphonamide and cyclizing by reaction with formic acid or ethyl formate; (b) chlorosulphonating a chloro-nitro aniline, e.g. 4-chloro-3-nitro-aniline, with chlorosulphonic acid in the presence of an alkali-metal halide, e.g. sodium chloride, to give a corresponding aniline-o-sulphonyl chloride, heating with a C1-5 alkylamine, cyclizing the resulting aniline-o-sulphonamide by heating with ethyl orthoformate, reducing the nitro group of the resulting benzothiadiazine with simultaneous removal of the halogen atom, e.g. by catalytic hydrogenation, chlorosulphonating and reacting with ammonia to give a product having an amino and sulphamoyl substituent in the benzene ring; or (c) chlorosulphonating a chloro-nitro-aniline to give an o-sulphochloride, reacting with a C1-5 alkylamine, heating the resulting aniline-o-sulphonamide with an aqueous solution of sodium sulphite to give a sodium amino-(N-alkylsulphamoyl)-nitrobenzene sulphonate, heating with chlorosulphonic acid, treating the resulting sulphochloride with ammonia and cyclizing the N - alkylsulphamoyl - nitro - sulphamoylaniline obtained by heating with ethyl orthoformate, followed by reduction of the nitro group to an amino group, if desired. Specification 826,921 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US891471XA | 1957-07-16 | 1957-07-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB891471A true GB891471A (en) | 1962-03-14 |
Family
ID=22215943
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21907/58A Expired GB891471A (en) | 1957-07-16 | 1958-07-08 | Benzothiadiazine compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB891471A (en) |
-
1958
- 1958-07-08 GB GB21907/58A patent/GB891471A/en not_active Expired
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