Réaction #1095

Équation de réaction

N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide

ethoxycarbonyl isothiocyanate

→

N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide

Rendement 75.0%

Solvants

ethyl acetate

DMF

Conditions de réaction

Traitement

1. 1
   Lavagewashed with 1N hydrochloric acid and water
2. 2
   SéchageThe organic phase is dried over magnesium sulfate
3. 3
   Autrethe solvent is removed by distillation
4. 4
   Autreprecipitated with heptane at -25° C
5. 5
   FiltrationThe precipitate is filtered off with suction
6. 6
   Autredried

Mode opératoire

1.20 g (4.0 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylaminobenzenesulfonamide is dissolved in 5 ml of anhydrous DMF, and 0.60 g (4.3 mmol) of 95% strength ethoxycarbonyl isothiocyanate is added. After 3 h at room temperature the mixture is taken up in ethyl acetate and washed with 1N hydrochloric acid and water. The organic phase is dried over magnesium sulfate and the solvent is removed by distillation. The residue is taken up in a little ethyl acetate and precipitated with heptane at -25° C. The precipitate is filtered off with suction and dried to give 1.29 g (75% of theory) of colorless N-tert-butyl-5-[N-(ethoxycarbonylaminothiocarbonyl)methylamino]-2-methoxycarbonylbenzenesulfonamide. m.p.: 110° C.

Source