GB595177A - Improvements in or relating to the manufacture of substituted sulphonamido compounds - Google Patents
Improvements in or relating to the manufacture of substituted sulphonamido compoundsInfo
- Publication number
- GB595177A GB595177A GB1171543A GB1171543A GB595177A GB 595177 A GB595177 A GB 595177A GB 1171543 A GB1171543 A GB 1171543A GB 1171543 A GB1171543 A GB 1171543A GB 595177 A GB595177 A GB 595177A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphate
- prepared
- compound
- ethyl alcohol
- mixture
- 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
- -1 sulphonamido compounds Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 235000019441 ethanol Nutrition 0.000 abstract 4
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic Effects 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- YAFKKDALCCJKSY-UHFFFAOYSA-N 2-ethylguanidine;sulfuric acid Chemical compound OS(O)(=O)=O.CCN=C(N)N YAFKKDALCCJKSY-UHFFFAOYSA-N 0.000 abstract 1
- WXDMRAWLKABMCM-UHFFFAOYSA-N 2-octylguanidine;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.CCCCCCCC[NH2+]C([NH3+])=N WXDMRAWLKABMCM-UHFFFAOYSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N benzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000001225 therapeutic Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Substituted sulphonamido compounds of therapeutic interest are formed by heating a benzenesulphonamide of the general formula <FORM:0595177/IV/1> or an alkali metal derivative thereof, with a compound, other than guanidine, of the type <FORM:0595177/IV/2> (X representing a chlorine or bromine atom, or an amino, or mono-acyl amino group; Y representing an alkyl, aryl or aralkyl radical, or an amino group; and R representing a hydrogen atom or alkyl, aryl or aralkyl radical), which may be generated in situ in the reaction-mixture by decomposing a salt thereof, e.g. the carbonate or sulphate, at a temperature generally within the approximate range 110 DEG to 200 DEG C., so as to eliminate a compound of the formula R.NH2. The process may be effected in the presence of a solvent or diluent, e.g. ethylene glycol, of boiling-point not less than the temperature of reaction. The reaction yields a compound of the general formula <FORM:0595177/IV/3> with elimination of the compound R.NH2, or may produce this derivative together with a compound of the general formula <FORM:0595177/IV/4> each of these types existing in their corresponding tautomeric forms. Numerous examples are given. Ethylguanidine sulphate is prepared by refluxing methyl iso-thiourea sulphate, water and alcoholic ethylamine solution. o-4-Xylylguanidine sulphate is prepared by heating a well-ground mixture of o-4-xylidine and methyl iso-thiourea sulphate, triturating the cooled melt with 95 per cent ethyl alcohol and standing for 10-12 hours. o-4-Xylylguanidine carbonate is prepared by treating with sodium hydroxide solution an aqueous solution of crude o-4-xylylguanidine sulphate and extracting with chloroform. Nonamidine hydrochloride is prepared by treating a mixture of nononitrile and dry ethyl alcohol with dry hydrogen chloride and then refrigerating for 3 days to crystallise noniminoethyl-ether hydrochloride; dry ethyl alcohol is stirred in, followed by dry alcoholic ammonia solution and the mixture maintained at 30-40 DEG C. for 36 hours, prior to evaporating the filtrate to dryness and recrystallizing the residue. n-Octylguanidine sulphate is prepared by refluxing together methyl iso-thiourea sulphate, n-octylamine, water and ethyl alcohol until methyl mercaptan is no longer evolved.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595177A true GB595177A (en) | 1947-11-28 |
Family
ID=1711498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1171543A Expired GB595177A (en) | 1943-07-19 | Improvements in or relating to the manufacture of substituted sulphonamido compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595177A (en) |
-
1943
- 1943-07-19 GB GB1171543A patent/GB595177A/en not_active Expired
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