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

HRID 1809159ノート

反応式

HRID 1809159 の反応式
[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

参加物

8

反応物 6

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

生成物 1

HCID 8561923-(1H-tetrazol-1-yl)phenol収率 72%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-334a0d7c27cc40868febf5eb42c1984a
出典データセット
uspto-grants-2013_01
特許番号
US08362017B2

反応ノート

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