Réaction #862

Équation de réaction

2-(2-hydroxyethoxy)ethylguanidine succinate

acetate

acetic anhydride

→

title compound

Rendement 40.0%

2-(2-guanidinoethoxy)ethyl acetate

Rendement 40.0%

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   AutreAfter the upper phase was removed by decantation
2. 2
   Autrethe obtained crude product
3. 3
   Lavagewas washed five times with 50 ml of diethylether
4. 4
   AutreThe product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid)

Mode opératoire

2.06 g (9.99 mmol) of 2-(2-hydroxyethoxy)ethylguanidine succinate, 8 ml of triethylamine, 0.122 mg (1.0 mmol) of 4-N,N-dimethylaminopyridine and 1.02 g (9.99 mmol) of acetic anhydride were placed in a 50 ml two neck flask and were stirred for 1 hour at room temperature. After the upper phase was removed by decantation, the obtained crude product was washed five times with 50 ml of diethylether. The product was purified by a silica gel column chromatography (eluent, chloroform/ethanol=2/1 containing 0.5% acetic acid) to obtain 1.00 g of the title compound (starch syrup-like, 4.0 mmol, 40.0% in yield) in the form of acetate. Results of the analysis of this compound are as follows.

Source