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

HRID 1626962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626962
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%)

Quellen und Nachweise

ORD-Eintrag
ord-e19530c1971f49768e42c0c539596957
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785481B2

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