Tolazamide
Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family.
Synthesis
The reaction between p-toluenesulfonamide and ethyl chloroformate in the presence of base gives tosylurethane . Heating that intermediate with azepane leads to the displacement of the ethoxy group and the formation of tolazemide.Azepane proper would lead to .