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

HRID 872270Notes

Reaction equation

HRID 872270 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (2-4, 150 mg, 0.734 mmol, 1.0 equv.) 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 then 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 with normal phase silica gel chromatography (EtOAc/hexane gradient from 0 to 100%) to yield 1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (2-5 LRMS m/z (M+H) 206.0 found, 206.1 required.

Workup

  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 with normal phase silica gel chromatography (EtOAc/hexane gradient from 0 to 100%)

Sources & evidence

ORD record
ord-9a061f09641d40969f600d464f17addb
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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