GB508794A - Manufacture of chloro-methyl compounds of sulphonamides - Google Patents
Manufacture of chloro-methyl compounds of sulphonamidesInfo
- Publication number
- GB508794A GB508794A GB21138A GB21138A GB508794A GB 508794 A GB508794 A GB 508794A GB 21138 A GB21138 A GB 21138A GB 21138 A GB21138 A GB 21138A GB 508794 A GB508794 A GB 508794A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphonamide
- chloride
- hydrogen chloride
- paraformaldehyde
- reacted
- 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
- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Abstract
508,794. Sulphonamide derivatives. GROVES, W. W. (I. G. Farbenindustrie Akt.- Ges.) Jan. 4, 1938, No. 211. [Class 2 (iii)] Chloromethyl compounds of sulphonamides are manufactured by causing a sulphonamide which has at least one exchangeable hydrogen atom at the amide nitrogen and also contains a hydrocarbon radicle having at least 4 carbon atoms, which may contain, substituents and /or may be interrupted by at least one oxygen, sulphur of nitrogen atom, to react with formaldehyde or a polymer thereof and hydrogen. chloride at ordinary or raised temperature, or by causing. hydrogen chloride to react with a methylol compound obtained by the reaction of formaldehyde or a polymer thereof with a sulphonamide as denned above. Suitable sulphonamidea are : butytsulphonamide, isohexylsulphomethylamide; dodecylsulphonamide, octadecylsulphonamide, chloroctadecylsulphonamide (obtained by the simultaneous action of sulphur dioxide and chlorine on n-octadecane, the chlorine being caused to act until in addition to that in the sulphochloride group a further chlorine atom has entered the carbon chain, and treatment of the. chloroctadecylsulphochloride with ammonia), 9 : 10-dichloroctadecyl: sulphomethylamide (obtained by splitting up oleylisothiourea, obtained from oleyl chloride-. and thiourea, with chlorine and treating the resulting 9: 10-dichloroctadecylsulphochloride with methylamine), p - butylphenoxyethanesulpho-N-n-hexylamide (obtained by treating the chloride of p-butylphenoxyethanesulphonic acid, obtained by condensing sodium p-butylphenolate. with the sodium salt of chlorethanesulphonic acid, with n-hexylamine), p-toluenesulphonamide and p - butylbenzenesulphonamide. The reaction may be carried out by dissolving or suspending the sulphonamide in aqueous formaldehyde and saturating with hydrogen chloride, or by dissolving the sulphonamide in, an. organic solvent, e.g. benzene, toluene, xylene, methylene chloride, carbon tetrachloride, chlorobenzene or ether, adding solid formaldehyde and introducing hydrogen chloride. The products may be used for the treatment of materials such as textiles, leather, paper or plasticmasses. In examples : (1) octadecylsulphonamide (obtainable by the action of liquid ammonia, on octadecylsulphochloride) is dissolved in methylene chloride, paraformaldehyde is added and hydrogen chloride introduced into the cold solution ; (2) a larger proportion of paraformaldehyde is employed in the process of (1): y (3) isohexylsulphomethylamide (obtamed by condenising isohexyl chloride with thiourea, converting the product into the sulphochloride and reacting this with liquid monomethylamine) is reacted with paraformaldehyde and hydrogen chloride in carbon octadecylsulphomethylolamide is treated with hydrogen chloride in : methylene chloride; (5) a hydrocarbon fraction obtained in the hydrogenation of carbon monoxide and containing about 14 carbon atoms is treated with sulphur dioxide and chlorine with exposure to ultra-violet light,- the sulphochloride, obtained is treated with liquid ammonia and the resulting sulphonamide in material may be replaced by hard paraffin ; (6) tetradecylsulphonamide, obtained as in (5), is mixed with aqueous formaldehyde and hydrogen chloride is introduced; (7) n-propyl-N-octadecylsulphonamide (obtained by reacting n, propylsulphochloride with octadecylamine) is reacted with paraformaldehyde and hydrogen chloride in benzene; (8) p-toluenesulphomethylolamide is treated with hydrogen chloride in chlorobenzene; (9) 1-stearylemino-2-nitro- _ benzene-4-sulphonamide (obtained by, acylating 1 - amino - 2-nitrobenzene-4-sulphonamide with stearic acid chloride) is reacted with paraformaldehyde and hydrogen chloride in methylene chloride; (10) 1-methoxy-2-nitrobenzene-4-sulphonamide is similarly reacted (11) p-isododecylcyclohexanol is condensed with sodium chlorethanesulphonate, the product is treated with phosphorus pentachloride and then with liquid ammonia, and the resulting sulphonamide is reacted with paraformaldehyde and hydrogen chloride in ether.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB21138A GB508794A (en) | 1938-01-04 | 1938-01-04 | Manufacture of chloro-methyl compounds of sulphonamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB21138A GB508794A (en) | 1938-01-04 | 1938-01-04 | Manufacture of chloro-methyl compounds of sulphonamides |
Publications (1)
Publication Number | Publication Date |
---|---|
GB508794A true GB508794A (en) | 1939-07-04 |
Family
ID=9700360
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21138A Expired GB508794A (en) | 1938-01-04 | 1938-01-04 | Manufacture of chloro-methyl compounds of sulphonamides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB508794A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3238257A (en) * | 1960-10-10 | 1966-03-01 | Du Pont | N-tertiary-alkyl alkanesulfonamides |
-
1938
- 1938-01-04 GB GB21138A patent/GB508794A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3238257A (en) * | 1960-10-10 | 1966-03-01 | Du Pont | N-tertiary-alkyl alkanesulfonamides |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB508794A (en) | Manufacture of chloro-methyl compounds of sulphonamides | |
US3641004A (en) | Alkyl esters of 6-(benzenesulfonyl)-trihalo-2-picolinic acid | |
GB819742A (en) | Derivatives of dialkyldithiophosphoric acids with a double amide function in the molecule and disinfesting compositions prepared from said compounds | |
Losanitch | LXXXIII.—Note on dithiocarbazinic acid | |
US2774749A (en) | Production of dicyandiamide-formaldehyde condensation products | |
US2721875A (en) | Method for preparing aminomethyl-sulfonic acids | |
US3126378A (en) | Novel polymeric thiadiazinethiones | |
US2349912A (en) | Halogen methyl compounds of sulphonamides and sulphonhydrazides and a process of preparing them | |
US3049559A (en) | Ureas | |
US2206273A (en) | Production of alkylene imines | |
US2524054A (en) | Preparation of guanidine salts | |
US2183929A (en) | Chx c ch | |
US2843602A (en) | 2, 3-di(chloroalkoxy)-p-dioxanes | |
US3038009A (en) | N-(beta, beta, beta-trinitroethyl)-4, 4, 4-trinitrobutyramide | |
GB808638A (en) | Organic phosphoric acid triamides | |
US3227762A (en) | Production of n-trisubstituted borazanes | |
US3143552A (en) | Reaction products of nitriles and sulfur trioxide | |
Daminev et al. | Chemical Utilization of Piperylene | |
US3035062A (en) | N, n'-di(2, 2, 2-trinitroethyl) ethylene urea and method of production | |
GB1359251A (en) | N-carbamoyl-or n-thiocarbamoyl - 4,5,6,7 - tetrahydrobenztriazoles processes for their preparation and their use as insecticides and acaricides | |
GB902058A (en) | Process for the preparation of di-benzoxazolyl-ethylene compounds | |
US3245875A (en) | Fungicidal method and composition involving polymeric thiadiazinethione compounds | |
GB507207A (en) | Manufacture of hydrohalides of substituted iso-thioureas | |
GB1447182A (en) | Thiadiazole substituted triazines | |
GB552987A (en) | Improvements in and relating to sulphur compounds |