Sulfuric Acid → 1-(1,1-dimethylethyl)-5-(2-methoxyphenyl)-2H-tetrazole

HRID 36032Notes

Reaction equation

HRID 36032 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]=[N:11][NH:12][N:13]=1.[CH3:14][C:15](O)([CH3:17])[CH3:16].S(=O)(=O)(O)O.[OH-].[K+]>C(O)(C(F)(F)F)=O.C(OCC)(=O)C>[CH3:14][C:15]([N:13]1[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[N:10][NH:11][NH:12]1)([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 8589085-(2-Methoxyphenyl)-1H-tetrazole

Product 1

HCID 193719111-(1,1-dimethylethyl)-5-(2-methoxyphenyl)-2H-tetrazoleYield 35.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(2-methoxyphenyl)-2H-tetrazole (0.83 g, 4.71 mmol), 2-methyl-2-propanol (0.7 g, 9.4 mmol), and sulfuric acid (0.24 g, 2.4 mmol) in 4.6 mL of TFA was stirred under nitrogen at room temperature for 16 hours. The reaction mixture then was diluted with ethyl acetate, poured into 2 M potassium hydroxide, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated. Purification of the residue by column chromatography on silica gel (elution: 10% ethyl acetate/hexane) gave 1-(1,1-dimethylethyl)-5-(2-methoxyphenyl)-2H-tetrazole (0.5102 g, 1.67 mmol), as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the residue by column chromatography on silica gel (elution: 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0c15ed0ab19c4ca5acabaf5106cb8789
Source dataset
uspto-grants-1995_05
Patent number
US05412102

Reaction notes

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