Reaction #80696

Reaction equation

2-aminoethanethiol

triethylamine

ethyl 2,3-dibromopropionate

chloroform toluene

→

title product

Ethyl 3-thiomorpholinecarboxylate

Solvents

chloroform

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Concentrationconcentrated in vacuo
3. 3
   Otherto obtain an orange liquid
4. 4
   workup.DISTILLATIONdistilled

Procedure

A warm solution of 2-aminoethanethiol (10.0 g, 0.130 mol) and triethylamine (36 mL, 0.260 mol) in chloroform is added over 5 minutes to a solution of ethyl 2,3-dibromopropionate (33.9 g, 0.130 mol) in a chloroform/toluene (1:1.6) solution. The reaction mixture is stirred at room temperature for 2.5 hours, filtered and concentrated in vacuo to obtain an orange liquid. The liquid is vacuum distilled to give the title product as a colorless liquid, bp 121°-124° C. at 3 mm Hg.

Source