Methyl iodide → 2-methyl-5-(4-nitrophenyl)-2H-tetrazole

HRID 1924942Notes

Reaction equation

[H-].[Na+].[CH3:3]I.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[CH:10][CH:9]=1)([O-:7])=[O:6]>CN(C=O)C>[CH3:3][N:16]1[N:17]=[N:18][C:14]([C:11]2[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=2)=[N:15]1.[CH3:3][N:15]1[C:14]([C:11]2[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=2)=[N:18][N:17]=[N:16]1

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred solution of 60% NaH (0.116 g, 2.89 mmol) and MeI (0.196 mL, 3.15 mmol) in DMF (2 mL) (cooled to 0° C., under N2) is added dropwise, a solution of 5-(4-nitrophenyl)-1H-tetrazole (0.502, 2.63 mmol) in DMF (7 mL). The reaction mixture is stirred under N2 for 1 hour and 30 min at 5° C. and then quenched with water and extracted with EtOAc. The organic layers are combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated to give a residue purified by silica gel column chromatography. Elution with 80:20 followed by 60:40 petroleum ether-EtOAc affords 2-methyl-5-(4-nitro-phenyl)-2H-tetrazole (0.265 g, 49%) as a white solid and 1-methyl-5-(4-nitro-phenyl)-1H-tetrazole (37.7 mg, 7%) as a yellow solid. The isomers are identified by NOE experiments.

Workup

customquenched with water
extractionextracted with EtOAc
washwashed with sat. NaCl
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customto give a residue
custompurified by silica gel column chromatography
washElution with 80:20

Sources & evidence

ORD record: ord-eb02f9ef502c48d78ea4f450b5a357e0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178530B2

Reaction notes

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