Reaction #88847

Reaction equation

H2S

sodium ethoxide

(EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—Cl

→

(EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—SH

Yield 99.0%

Solvents

ethanol

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONis added, by metered addition at 52° C.
2. 2
   Filtrationthe suspension is filtered
3. 3
   OtherThe filtrate is freed of the solvent on a rotary evaporator
4. 4
   Otherdried under reduced pressure

Procedure

To a solution of NaSH in ethanol [prepared by introducing H2S (15.21 g, 0.45 mol, 1.07 eq) into a sodium ethoxide solution (prepared from Na (10.55 g, 0.46 mol, 1.10 eq) in EtOH (300 mL))] is added, by metered addition at 52° C., (EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—Cl (138.90 g, 0.42 mol, 1.00 eq) in ethanol (300 ml), and the mixture is heated to 78° C. After a reaction time of 5 h, the mixture is cooled to room temperature and the suspension is filtered. The filtrate is freed of the solvent on a rotary evaporator and dried under reduced pressure. The (EtO)3Si—CH2CH2CH2—NH—CO—NH—CH2CH2—SH product (134.96 g, 97.9% of theory) is obtained as a white solid.

Source