Reaktion #1095

Reaktionsgleichung

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

ethoxycarbonyl isothiocyanate

→

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

Ausbeute 75.0%

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 1N hydrochloric acid and water
2. 2
   TrocknenThe organic phase is dried over magnesium sulfate
3. 3
   Sonstigethe solvent is removed by distillation
4. 4
   Sonstigeprecipitated with heptane at -25° C
5. 5
   FiltrationThe precipitate is filtered off with suction
6. 6
   Sonstigedried

Vorschrift

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.

Quelle