Methyl iodide → 5-[4-(benzyloxy)phenyl]-2-methyl-2H-tetrazole

HRID 4945Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:19][N:18]=[N:17][N:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20]CN(C(C)C)C(C)C.CI>CN1C(=O)CCC1.O>[CH3:20][N:18]1[N:17]=[N:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)=[N:19]1

Participants

Conditions

Temperature: 18 °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.

Workup

temperaturecooled to 18° C
customThe resulting solid was collected
washwashed with water
customrecrystallized from ethanol
customdried in vacuo at 50° C.

Sources & evidence

ORD record: ord-05c3ddf43a57421683e130c85cd4575d
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05242924

Reaction notes

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