butyl N-hydroxycarbamate

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 26.6 Parts of butyl N-hydroxycarbamate and 38.1 parts of p-toluenesulphonylchloride are stirred in 100 parts of dioxan maintained at 0° to 5° C. 20.4 Parts of triethylamine are added during 1 hour keeping the pH at 3 to 6. The mixture is then stirred for 18 hours at 25° C and added to 500 parts of water. The oily precipitate is taken up into 200 parts toluene, and the solution is dried, filtered and evaporated to constant weight at 40° C under reduced pressure to give 52 parts of butyl N-p-toluenesulphonyloxycarbamate as a yellow oil. maintained at 0° to 5° C the solution is dried filtered evaporated to constant weight at 40° C under reduced pressure

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 26.6 Parts of butyl N-hydroxycarbamate and 38.1 parts of p-toluenesulphonylchloride are stirred in 100 parts of dioxan maintained at 0° to 5° C. 20.4 Parts of triethylamine are added during 1 hour keeping the pH at 3 to 6. The mixture is then stirred for 18 hours at 25° C and added to 500 parts of water. The oily precipitate is taken up into 200 parts toluene, and the solution is dried, filtered and evaporated to constant weight at 40° C under reduced pressure to give 52 parts of butyl N-p-toluenesulphonyloxycarbamate as a yellow oil. maintained at 0° to 5° C the solution is dried filtered evaporated to constant weight at 40° C under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: With respect to butyl N,O-dimethylcarbamate, a process disclosed in the specification of West German Patent Application Laid-open No. 3,245,503 is known. This process comprises reacting sulfate of hydroxylamine as a starting material with butyl chloroformate in the presence of sodium hydroxide, extracting the reaction product with dichloromethane, drying the extract, distilling the solvent away from the dried extract to obtain butyl hydroxycarbamate and dimethylating this product using dimethyl sulfate and a sodium hydroxide solution to obtain ethyl N,O-dimethylhydroxycarbamate in the total yield of 65%. extracting the reaction product with dichloromethane drying the extract distilling the solvent away from the dried extract

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: DE3245503 discloses a process for producing methoxymethylamine via butyl N,O-dimethylcarbamate as an intermediate. According to this prior art process, the starting material hydroxylamine sulfate is allowed to react with butyl chloroformate in the presence of sodium hydroxide to form butyl hydroxycarbamate which is then subjected to the steps of extraction with dichloromethane and of drying, and after the solvent is distilled off, said butyl hydroxycarbamate is dimethylated with dimethyl sulfate in an aqueous solution of sodium hydroxide, followed by hydrolysis with hydrochloric acid, whereby methoxymethylamine hydrochloride is obtained in 65% yield.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 26.6 Parts of butyl N-hydroxycarbamate and 38.1 parts of p-toluenesulphonylchloride are stirred in 100 parts of dioxan maintained at 0° to 5° C. 20.4 Parts of triethylamine are added during 1 hour keeping the pH at 3 to 6. The mixture is then stirred for 18 hours at 25° C and added to 500 parts of water. The oily precipitate is taken up into 200 parts toluene, and the solution is dried, filtered and evaporated to constant weight at 40° C under reduced pressure to give 52 parts of butyl N-p-toluenesulphonyloxycarbamate as a yellow oil. maintained at 0° to 5° C the solution is dried filtered evaporated to constant weight at 40° C under reduced pressure