Sulfuric Acid → HCID 14888666, compound

HRID 1721229Notes

Reaction equation

HRID 1721229 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)=[CH:4][CH:3]=1.[C:13](O)([CH3:16])([CH3:15])[CH3:14].S(=O)(=O)(O)O>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[N:11][N:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 2851645-(4-Methylphenyl)-1H-tetrazole

Product 1

HCID 14888666HCID 14888666, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(4-methylphenyl)-2H-tetrazole (W. G. Finnegan, R. A. Henry, R. Lofquist J. Am. Chem. Soc. 1958, 80, 3908.) (19.9 g, 0.12 mol), t-butanol (19.5 g, 0.26 mol) and concentrated sulfuric acid (5.84 g, 0.06 mol) in trifluoroacetic acid (122 mL) was stirred at room temperature (3 h) and then diluted with ethyl acetate (250 mL). The mixture was washed sequentially with water (2×50 mL), 10% aqueous sodium hydroxide until washings were basic, water (2×30 mL), and then dried over sodium sulfate (Na2SO4) and filtered. Following removal of the solvents in vacuo, the resultant oil was purified by HPLC on silica gel eluting with 20:1 mixture of hexanes-ethyl acetate to provide 17.5 g of 5-(4-methylphenyl)-2-(1,1-dimethylethyl)-2H-tetrazole as a clear oil, bp. 120°-122° C. (0.3 mm Hg).

Workup

  1. washThe mixture was washed sequentially with water (2×50 mL), 10% aqueous sodium hydroxide until washings
  2. dry with materialwater (2×30 mL), and then dried over sodium sulfate (Na2SO4)
  3. filtrationfiltered
  4. customremoval of the solvents in vacuo
  5. customthe resultant oil was purified by HPLC on silica gel eluting with 20:1 mixture of hexanes-ethyl acetate

Sources & evidence

ORD record
ord-8916e17ae446478bbbcd1efa8152f1b6
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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