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

HRID 129563

Reaction equation

HRID 129563 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 2M 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-c15cc2766e114b60bb4f63376968896d
Source dataset
uspto-grants-1995_11
Patent number
US05468867

Linked notes

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