Reaction #1810844

Reaction equation

4-iodophenylsulphonyl chloride

2-methoxyethylamine

triethylamine

→

title compound

Yield 100.1%

N-(2-Methoxyethyl)-4-iodobenzenesulphonamide

Yield 100.1%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   Temperatureto warm to ambient temperature
2. 2
   OtherThe solvent was removed by evaporation
3. 3
   workup.DISSOLUTIONthe resulting oil dissolved EtOAc (100 ml)
4. 4
   Washwashed with 0.33 M aqueous citric acid solution (2×100 ml), brine (100 ml)
5. 5
   Otherdried
6. 6
   OtherThe volatiles were removed by evaporation

Procedure

A solution of 4-iodophenylsulphonyl chloride (3.64 g, 12 mmol) in DCM (30 ml) was added dropwise to a solution of 2-methoxyethylamine (1.3 ml, 15 mmol) and triethylamine (2 ml, 15 mmol) in DCM (60 ml) cooled by an ice bath to 0° C. The mixture was then allowed to warm to ambient temperature and stirred for 1 hour. The solvent was removed by evaporation and the resulting oil dissolved EtOAc (100 ml) and washed with 0.33 M aqueous citric acid solution (2×100 ml), brine (100 ml) and dried. The volatiles were removed by evaporation to give the title compound (4.1 g, 100%) as a clear oil. NMR 3.12 (2H, q), 3.28 (3H, s), 3.44 (2H, t), 4.90 (1H, t), 7.57 (2H, d), 7.81 (2H, d); m/z: 342.

Source