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

HRID 1798823

반응식

HRID 1798823 반응식
[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

참가 물질

5

반응물 3

HCID 1118Sulfuric Acid2회HCID 5716394-(2H-1,2,3,4-tetrazol-2-yl)anilineHCID 23668193Sodium Nitrite

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매3회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-292ccee5c3cc461fb92753ecf69c3672
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343990B2

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