Reaction #2200611

Reaction equation

1-butylimidazole

O-mesitylene sulfonylhydroxylamine

ether

→

1-butyl-3-aminoimidazolium mesitylene sulfonate

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITto stand at −16° C. overnight
3. 3
   FiltrationThe product was recovered by filtration
4. 4
   Washwashed with a mixture of CH2Cl2: ether (3:1 v/v)
5. 5
   Otherto yield a white amorphous powder
6. 6
   OtherThe crude product was recrystallized from a mixture of CH2Cl2 (80 mL) and ether (80 mL)
7. 7
   Otherto give 12.40 g

Procedure

An ice-cold solution of 1-butylimidazole (7.0 g, 16.30 mmol) in anhydrous CH2Cl2 (35 mL) was treated dropwise with a solution of O-mesitylene sulfonylhydroxylamine (17.8 g, 16.50 mmol) in CH2Cl2 (70 mL). After stirring for 6 hours in the ice-bath, ether (210 mL) was added with stirring over the course of 1 hour. The resulting mixture was allowed to stand at −16° C. overnight. The product was recovered by filtration, and washed with a mixture of CH2Cl2: ether (3:1 v/v) to yield a white amorphous powder; 16.70 g. The crude product was recrystallized from a mixture of CH2Cl2 (80 mL) and ether (80 mL) to give 12.40 g; mp 71-73° C.

Source