Sodium Nitrite → 1-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

HRID 1626962ノート

反応式

HRID 1626962 の反応式
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11](N)=[CH:12][C:7]=2[N:6]=[N:5]1.N([O-])=[O:17].[Na+]>OS(O)(=O)=O.O>[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:7]=2[N:6]=[N:5]1

参加物

5

反応物 2

HCID 23668193Sodium NitriteHCID 686567951-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine

生成物 1

HCID 574249931-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

実験手順

To a solution of 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (9) (150 mg, 0.734 mmol, 1.0 equiv.) in 20% H2SO4 (5 mL), was slowly added sodium nitrite (70.8 mg, 1.026 mmol, 1.4 equiv.). The reaction mixture was stirred at room temperature until LCMS showed complete conversion to diazonium ion. The reaction solution was transferred to a microwave vial and irradiated at 120° C. for 50 minutes. LCMS showed complete hydrolysis of the diazonium salt. The reaction mixture was diluted with water, then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to give the crude product, which was purified via silica gel chromatography (EtOAc/Hexane gradient from 0 to 100%) to yield 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (10). LRMS m/z (M+H) 206.0 found, 206.1 required.

後処理

  1. customirradiated at 120° C. for 50 minutes
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified via silica gel chromatography (EtOAc/Hexane gradient from 0 to 100%)

出典と根拠

ORDレコード
ord-e19530c1971f49768e42c0c539596957
出典データセット
uspto-grants-2014_07
特許番号
US08785481B2

反応ノート

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