4-Aminophenol → 4-(1H-1,2,3,4-tetrazol-1-yl)phenol

HRID 376265ノート

反応式

HRID 376265 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](OC(OCC)OCC)C.[N-:19]=[N+:20]=[N-:21].[Na+]>C(O)(=O)C>[N:1]1([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH:9]=[N:21][N:20]=[N:19]1

参加物

5

反応物 3

HCID 4034-AminophenolHCID 31214Ethyl orthoformateHCID 33557Sodium Azide

生成物 1

HCID 5429104-(1H-1,2,3,4-tetrazol-1-yl)phenol収率 30%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of p-amino-phenol (0.1 mol) in glacial acetic acid (140 ml) at 70-75° under nitrogen atmosphere was added triethylorthoformate (0.1 mol). The mixture was stirred at this temperature for 4 h, then, sodium azide (0.32 mol) was added portionwise and the reaction was continued for 18 h, cooled to room temperature and poured into ice water (400 ml) and extracted with diethyl ether (3×400 ml) and ethyl acetate (1×400 ml), dried (MgSO4), filtered and concentrated to give a dark brown residue which was triturated with 200 ml of a mixture of ethanol:diethyl ether (1:1 v/v) and filtered to afford the title compound in 30% yield.

後処理

  1. waitthe reaction was continued for 18 h
  2. extractionextracted with diethyl ether (3×400 ml) and ethyl acetate (1×400 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark brown residue which
  7. customwas triturated with 200 ml of a mixture of ethanol:diethyl ether (1:1 v/v)
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-53f140dcf3da4e959a2ab144e43febf6
出典データセット
uspto-grants-2000_02
特許番号
US06020346

反応ノート

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