Reacción #1095

Ecuación de reacción

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

ethoxycarbonyl isothiocyanate

→

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

Rendimiento 75.0%

Disolventes

ethyl acetate

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 1N hydrochloric acid and water
2. 2
   SecadoThe organic phase is dried over magnesium sulfate
3. 3
   Otrothe solvent is removed by distillation
4. 4
   Otroprecipitated with heptane at -25° C
5. 5
   FiltraciónThe precipitate is filtered off with suction
6. 6
   Otrodried

Procedimiento

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.

Fuente