Sulfuric Acid → 4-(2H-Tetrazol-2-yl)phenol

HRID 1798823Notes

Reaction equation

HRID 1798823 reaction equation
[N:1]1[N:2]([C:6]2[CH:12]=[CH:11][C:9](N)=[CH:8][CH:7]=2)[N:3]=[N:4][CH:5]=1.S(=O)(=O)(O)[OH:14].N([O-])=O.[Na+]>O>[N:1]1[N:2]([C:6]2[CH:12]=[CH:11][C:9]([OH:14])=[CH:8][CH:7]=2)[N:3]=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 5716394-(2H-1,2,3,4-tetrazol-2-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 157603994-(2H-Tetrazol-2-yl)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

The crude 4-(2H-tetrazol-2-yl)aniline (60 mg, 0372 mmol) was suspended in water (2 mL) and sulfuric acid (0.2 mL) before cooling to 0° C. An aqueous solution of sodium nitrite (26 mg, 0.565 mmol) in water (2 mL) was added. The mixture was stirred at 0° C. for 30 min. Additional water (1 mL) and sulfuric acid (0.37 mL) was added and the mixture heated at 120° C. for 1 hour. The reaction was then cooled and extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, concentrated and purified by preparative TLC eluting with 30% ethyl acetate/hexanes to give the desired phenol product as yellow solid. LRMS calc: 162.1; obs: 163.2 (M+1).

Workup

  1. temperaturethe mixture heated at 120° C. for 1 hour
  2. temperatureThe reaction was then cooled
  3. extractionextracted 3 times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by preparative TLC
  9. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-292ccee5c3cc461fb92753ecf69c3672
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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