Methyl iodide → 2-Methyl-5-(3-nitrophenyl)-2H-tetrazole

HRID 1588040Notes

Reaction equation

HRID 1588040 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:18]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[N:12][N:13]([CH3:18])[N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2851295-(3-nitrophenyl)tetrazole

Product 1

HCID 140450862-Methyl-5-(3-nitrophenyl)-2H-tetrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Nitro-(1H-tetrazol-5-yl)benzene (0.99 g) was added at 0° C. to a magnetically stirred suspension of sodium hydride (243 mg, 60% oil dispersion) in 50 ml of dry tetrahydrofuran. The reaction mixture was stirred for 15 minutes and then iodomethane was added in 6 increments of 0.5 ml over a 3 hour period. The reaction mixture was concentrated in vacuo and the residue was partitioned between water (50 ml) and ethyl acetate. The aqueous layer was extracted (2×15 ml) with ethyl acetate and the combined organic extracts were washed with brine, dried, and concentrated. The title compound was obtained as a solid after flash chromatography on silica gel (chloroform-methanol, 95:5).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between water (50 ml) and ethyl acetate
  3. extractionThe aqueous layer was extracted (2×15 ml) with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-87d32d2ecf764901bfbe4b0c434af34d
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

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