Reaction #969898

Reaction equation

product

3-[(1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]-benzonitrile

DMSO

hydroxylamine hydrochloride

triethylamine

→

title product

3-[(1,1-dioxido-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepin-8-yl)oxy]-N′-hydroxybenzenecarboximidamide

Solvents

water

ethyl ether

dichloromethane

THF

Conditions

Workup

1. 1
   OtherAn abundant white precipitate is formed
2. 2
   workup.ADDITIONwhich is diluted
3. 3
   OtherThe THF is evaporated off under reduced pressure
4. 4
   Filtrationthe suspension is filtered
5. 5
   workup.STIRRINGthe solution is stirred overnight at ambient temperature
6. 6
   FiltrationThe solid is filtered off
7. 7
   Washrinsed with water and ethyl ether

Procedure

To 750 μl of DMSO there are added hydroxylamine hydrochloride (1.90 mmol) and then triethylamine (1.90 mmol). An abundant white precipitate is formed, which is diluted by adding 3 ml of THF and stirring is carried out for 25 minutes at ambient temperature. The THF is evaporated off under reduced pressure and the suspension is filtered. The product of Example 6 (0.317 mmol) is added to the filtrate and the solution is stirred overnight at ambient temperature. After adding water to the reaction mixture, a gum forms which is made solid by adding dichloromethane and ethyl ether. The solid is filtered off and rinsed with water and ethyl ether to yield the title product.

Source