Patent GB-457119-A (GB)
Title: Process for the manufacture of sulphamic acid fluorides
Filed: 1935-05-21
Abstract: Sulphamic acid fluorides of the formula RR<1>NSO2F, where R and R<1> are alkyl groups, which may be linked together to form a cycloaliphatic ring system and which may be substituted, are prepared by treating the corresponding sulphamic acid chlorides with a metal fluoride in the presence of a solvent or diluent.  Preferably, the reaction is effected at 70--100 DEG  C., in an aqueous medium with the use of a water-soluble fluoride. Examples are given in which (1) dimethylsulphamic acid chloride and potassium fluoride (or sodium fluoride or zinc fluoride) yield dimethylsulphamic acid fluoride; (2) diethylsulphamic acid fluoride is obtained similarly from the corresponding chloride. Sulphamic acid fluorides are similarly obtainable from the sulphamic acid chlorides of b , b <1>-dichlorodiethylamine, piperidine, morpholine, b -b <1>-dicyanodiethylamine, methylhexylamine. methyldodecylamine, methyl - b  - (methylamino) ethyl sulphide, N-methyl-b -phenylethylamine, and sarcosine methyl ester.  The products are useful for combating insect pests and other parasites.  The sulphamic acid chlorides specified above are obtainable from the corresponding secondary amines and sulphuryl chloride.ALSO:Sulphamic acid fluorides of the formula RR1NSO2F, where R and R1 are alkyl groups, which may be linked together to form a cycloaliphatic ring system and which may be substituted, are prepared by treating the corresponding sulphamic acid chlorides with a metal fluoride in the presence of a solvent or diluent.  Preferably, the reaction is effected at 70-100 DEG  C. in an aqueous medium with the use of a water-soluble fluoride.  Examples are given in which (1) dimethylsulphamic acid chloride and potassium fluoride (or sodium fluoride or zinc fluoride) yield dimethylsulphamic acid fluoride; (2) diethylsulphamic acid fluoride is obtained similarly from the corresponding chloride.  Sulphamic acid fluorides are similarly obtainable from the sulphamic acid chlorides of b ,b 1-dichlorodiethylamine, piperidine, morpholine, b ,b 1-dicyanodiethylamine, methylhexylamine, methyldodecylamine, methyl-p-(methylamino)ethyl sulphide, N-methyl-b -phenylethylamine, and sarcosine methyl ester.  The products are useful for combating insect pests and other parasites and for this purpose they may be used (a) in the gaseous phase, alone or with other inert or active gases, such as carbon dioxide, carbon monoxide, ethylene oxide or hydrocyanic acid, and with or without a warning or irritating substance such as ethyl chloroformate, (b) in the form of sprayed or nebulized solutions or dispersions, e.g., in water or a low-boiling solvent such as carbon tetrachloride, acetone, benzene or benzine, or unsaturated solvents obtained in petroleum fractionation; other active substances such as nicotine may be added to the solutions or dispersions; the solutions may also be absorbed in paper or other porous substance; or (c) in a solid or pasty form, alone or with appropriate additions, e.g. talc or chalk.  The sulphamic acid chlorides specified above are obtainable from the corresponding secondary amines and sulphuryl chloride.