Acetic Acid → 3-(1H-tetrazol-1-yl)phenol

HRID 1809159노트

반응식

HRID 1809159 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(OCC)(OCC)OCC.[N-:19]=[N+:20]=[N-:21].[Na+].[C:23](O)(=O)C.Cl.N([O-])=O.[Na+]>O>[N:1]1([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH:23]=[N:21][N:20]=[N:19]1

참가 물질

8

반응물 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 115683-AminophenolHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 23668193Sodium Nitrite

생성물 1

HCID 8561923-(1H-tetrazol-1-yl)phenol수율 72%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a 200 ml round bottom flask equipped with a magnetic stir bar containing a solution of 3-aminophenol (5 g, 45.8 mmol, 1.0 eq) in triethyl orthoformate (24.4 ml, 146.5 mmol, 3.2 eq) was added sodium azide (3.73 g, 57.3 mmol, 1.25 eq) and acetic acid (41.95 ml, 732.8 mmol, 16.0 eq). The mixture was stirred for 10 min at room temperature and then heated at 80° C. for 1.5 h. After heating, the mixture was bronze and homogeneous. The mixture was cooled to room temperature. Water (30 mL) and 6 N HCl (17 mL) was added. A 25% aqueous solution of NaNO2 (6 mL) was slowly added while the reaction mixture was cooled in an ice bath. A white solid, 3-tetrazol-1-yl-phenol 29 (5.3 g, 72% yield) was obtained upon filtration and washing with water. LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 163.0 (M+H)+1 1H-NMR, Varian 400 MHz (MeOH-d4) δ 9.71 (s, 1H), 7.41 (t, 1H), 7.28 (d, 2H), 6.96 (d, 1H) ppm.

후처리

  1. customTo a 200 ml round bottom flask equipped with a magnetic stir bar
  2. temperatureheated at 80° C. for 1.5 h
  3. temperatureAfter heating
  4. temperatureThe mixture was cooled to room temperature
  5. temperaturewas cooled in an ice bath

출처 및 근거

ORD 기록
ord-334a0d7c27cc40868febf5eb42c1984a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362017B2

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