Reaction #1095

Reaction equation

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

ethoxycarbonyl isothiocyanate

→

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

Yield 75.0%

Solvents

ethyl acetate

DMF

Conditions

Workup

1. 1
   Washwashed with 1N hydrochloric acid and water
2. 2
   DryingThe organic phase is dried over magnesium sulfate
3. 3
   Otherthe solvent is removed by distillation
4. 4
   Otherprecipitated with heptane at -25° C
5. 5
   FiltrationThe precipitate is filtered off with suction
6. 6
   Otherdried

Procedure

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