Reaction #4581

Reaction equation

2-hydroxybenzenesulfonamide

potassium carbonate

methyl 2-bromopropionate

→

2-(1-methoxycarbonylethoxy)- benzenesulfonamide

Yield 80.7%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturethe suspension is then heated for 5 hours to 45° C
2. 2
   TemperatureAfter the reaction mixture has cooled
3. 3
   Otherthe precipitated salts are isolated
4. 4
   Concentrationthe filtrate is concentrated in vacuo
5. 5
   OtherThe residue is recrystallised from ethanol

Procedure

34.6 g of 2-hydroxybenzenesulfonamide and 55.3 g of potassium carbonate are added to 800 ml of acetonitrile. With efficient stirring, 33.4 g of methyl 2-bromopropionate are added dropwise over 10 minutes and the suspension is then heated for 5 hours to 45° C. After the reaction mixture has cooled, the precipitated salts are isolated and the filtrate is concentrated in vacuo. The residue is recrystallised from ethanol, affording 41.8 g of 2-(1-methoxycarbonylethoxy)- benzenesulfonamide with a melting point of 140°-142° C.

Source