GB589040A - Improvements in or relating to the production of sulphonamides - Google Patents
Improvements in or relating to the production of sulphonamidesInfo
- Publication number
- GB589040A GB589040A GB1092944A GB1092944A GB589040A GB 589040 A GB589040 A GB 589040A GB 1092944 A GB1092944 A GB 1092944A GB 1092944 A GB1092944 A GB 1092944A GB 589040 A GB589040 A GB 589040A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- sulphonamide
- produced
- alkyl
- derivative
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Sulphonamide derivatives are produced by heating together in the liquid phase an aryl sulphonamide containing at least one free hydrogen atom in the sulphonamide grouping and a thioether of the general formula R2SR3 wherein R2 is an alkyl or aralkyl group and R3 is a heterocyclic group containing at least one nuclear nitrogen atom. Reaction may be effected in the presence of a basic metal oxide or hydroxide, particularly those of Groups Ia, IIa and IVb of the Periodic Table, or of a salt thereof with an acid replaceable by a sulphonamido group, or of a strong organic base. Specified compounds are sodium and potassium hydroxides, magnesium oxide, barium hydroxide, sodium, potassium and lead carbonates and acetates, triethanolamine, trimethylamine and sodium ethoxide. A high-boiling solvent, e.g. phenol, the alkylated phenols, and the naphthols or mixtures thereof may be present. The groups R2 and R3 are preferably so chosen that the mercaptan obtained as a by-product or the sulphonamide produced is progressively removed from the reaction zone, and R2 represents preferably an alkyl group containing not more than six carbon atoms, advantageously methyl, ethyl, propyl or isopropyl. The sulphonamide may be unsubstituted, e.g. benzene- or p-toluene sulphonamide, or monosubstituted, having the general formula R.SO2NHR1, wherein R1 is an alkyl, aryl, acyl, aralkyl or heterocyclic group. Specified as mono-alkylated compounds are N-methyl and N-ethyl sulphonamides, and as monoacyl compounds, a sulphonacetamide or a sulphonpropionamide. When R1 represents a heterocyclic group a sulphonamide derivative may be produced containing two like or unlike heterocyclic groups, e.g. a thiazole with a pyrimidine group. R3 may be a pyridine, diazine (e.g. a pyrimidine), thiazole, thiazoline, or oxazole group, optionally containing substituents. The group R in the sulphonamide may represent phenyl containing as a p-substituent an amino group, free or protected, i.e. an acylamino or alkylamino group, or a group readily convertible to amino, i.e. a nitro or azo group, or a halogen atom. The thioether may be produced in situ either prior to or simultaneously with the desired sulphonamide derivative, e.g. by interacting an alkali metal mercaptan derivative with a halogen derivative of the appropriate heterocyclic compound, or, in the case of a pyrimidine thioether, from an S-alkyl isothiourea and an appropriately substituted diketone. Numerous examples are given. Lead sulphanilamide is prepared by the interaction of sulphanilamide and lead acetate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1092944A GB589040A (en) | 1944-06-07 | 1944-06-07 | Improvements in or relating to the production of sulphonamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1092944A GB589040A (en) | 1944-06-07 | 1944-06-07 | Improvements in or relating to the production of sulphonamides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB589040A true GB589040A (en) | 1947-06-10 |
Family
ID=9976908
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1092944A Expired GB589040A (en) | 1944-06-07 | 1944-06-07 | Improvements in or relating to the production of sulphonamides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB589040A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2652395A (en) * | 1951-06-21 | 1953-09-15 | Olin Mathieson | N-(c mercapto-pyrimidyl)-p-aminobenzenesulfonamides |
US2703800A (en) * | 1951-09-10 | 1955-03-08 | Chemie Linz Ag | Process of producing n1-heterocyclically substituted benzene-sulfonic acid amides |
US3155650A (en) * | 1961-03-03 | 1964-11-03 | Mead Johnson & Co | 2-substituted-4-sulfanilamidoquinazolines and process |
DE1201844B (en) * | 1960-05-12 | 1965-09-30 | Mead Johnson & Co | Process for the preparation of 4-sulfanilamidoquinazoline derivatives substituted in the 2-position |
US20110144179A1 (en) * | 2008-09-03 | 2011-06-16 | Schwartz Martin A | Substituted Heterocyclic Mercaptosulfonamide Metalloprotease Inhibitors |
-
1944
- 1944-06-07 GB GB1092944A patent/GB589040A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2652395A (en) * | 1951-06-21 | 1953-09-15 | Olin Mathieson | N-(c mercapto-pyrimidyl)-p-aminobenzenesulfonamides |
US2703800A (en) * | 1951-09-10 | 1955-03-08 | Chemie Linz Ag | Process of producing n1-heterocyclically substituted benzene-sulfonic acid amides |
DE1201844B (en) * | 1960-05-12 | 1965-09-30 | Mead Johnson & Co | Process for the preparation of 4-sulfanilamidoquinazoline derivatives substituted in the 2-position |
US3155650A (en) * | 1961-03-03 | 1964-11-03 | Mead Johnson & Co | 2-substituted-4-sulfanilamidoquinazolines and process |
US20110144179A1 (en) * | 2008-09-03 | 2011-06-16 | Schwartz Martin A | Substituted Heterocyclic Mercaptosulfonamide Metalloprotease Inhibitors |
US8404866B2 (en) * | 2008-09-03 | 2013-03-26 | Florida State University Research Foundation | Substituted heterocyclic mercaptosulfonamide metalloprotease inhibitors |
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