Reaction #2122518

Reaction equation

Compound 20

N,N-dihexyl-2-methylbenzo[d]thiazole-6-sulfonamide

p-toluenesulfonic acid methyl ester

hexane

→

Compound 21

Yield 78.9%

6-(N,N-dihexylsulfamoyl)-2,3-dimethylbenzo[d]-thiazole-3-ium tosylate

Yield 78.9%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   OtherA sticky dark brown solid separated which
3. 3
   Washwas washed with hexane
4. 4
   Otherdried under vacuum

Procedure

A mixture of Compound 20 (2.0 g, 5.0 mmol) and p-toluenesulfonic acid methyl ester (1.4 g, 7.5 mmol) was heated in a pressure tube at 130° C. for 2 hours. The mixture was allowed to cool to room temperature, and the resulting mass was dissolved in ethyl acetate (4 ml). The combined mixture was then added drop wise to hexane (40 ml). A sticky dark brown solid separated which was washed with hexane and dried under vacuum to yield 2.3 g (78%) of Compound 21 which was used without any further purification. The structure of this compound is given below:

Source