Reaction #5041

Reaction equation

methyl iodide

tetrazole

5-(4-benzyloxyphenyl)tetrazole

DIPEA

→

2-methyl-5-(4-benzyloxyphenyl)-2H-tetrazole

Solvents

NMP

NMP

water

water

Conditions

Workup

1. 1
   Temperaturecooled to 18° C
2. 2
   OtherThe resulting solid was collected
3. 3
   Washwashed with water
4. 4
   Otherrecrystallized from ethanol
5. 5
   Otherdried in vacuo at 50° C.

Procedure

To a stirred solution containing 337 g of the tetrazole and 362 mL of DIPEA in 1 L of NMP cooled to 18° C. under N2 was added dropwise over 1.5 hrs 200 g of methyl iodide in 170 mL NMP. After stirring an additional hour at room temperature, the reaction mixture was diluted with 340 mL of water and the reaction mixture was diluted with 340 mL of water and cooled to 18° C. The resulting solid was collected, washed with water, recrystallized from ethanol and dried in vacuo at 50° C. to give 232.3 g of 2-methyl-5-(4-benzyloxyphenyl)-2H-tetrazole.

Source