Reaction #1726731

Reaction equation

water

1-(5-hydroxy-1H-benzimidazol-2-yl)-3-(2-methoxyethyl)urea

2,6-dichlorobenzenesulfonyl chloride

→

2-{[(2-methoxyethyl)carbamoyl]amino}-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate

Solvents

sodium hydroxide

Conditions

Workup

1. 1
   workup.ADDITIONare then added
2. 2
   FiltrationThe precipitate is filtered off by suction
3. 3
   Washwashed with three times 2 cm3 of water
4. 4
   Dryingdried under reduced pressure (13 kPa) over phosphorus pentoxide

Procedure

To a solution of 175 mg of 1-(5-hydroxy-1H-benzimidazol-2-yl)-3-(2-methoxyethyl)urea in 15 cm3 of 0.1N aqueous sodium hydroxide solution are added 189 mg of finely ground 2,6-dichlorobenzenesulfonyl chloride. The suspension is stirred for about 20 hours at a temperature in the region of 20° C., 10 cm3 of water are then added and the mixture is cooled to about 5° C. for about 15 minutes. The precipitate is filtered off by suction, washed with three times 2 cm3 of water and dried under reduced pressure (13 kPa) over phosphorus pentoxide. After flash chromatography on a column of silica [eluent: dichloromethane/methanol/acetonitrile (95/3/2 by volume)], 65 mg of 2-{[(2-methoxyethyl)carbamoyl]amino}-1H-benzimidazol-5-yl 2,6-dichlorobenzenesulfonate are obtained in the form of a cream-coloured powder, the characteristics of which are as follows:

Source