Pyridiniumtribromide → 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine

HRID 1618926Notes

Reaction equation

HRID 1618926 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[N:6]=[N:5]1.[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:16][C:12]1[C:7]2[N:6]=[N:5][N:4]([CH2:3][C:2]([CH3:15])([CH3:14])[CH3:1])[C:8]=2[CH:9]=[CH:10][C:11]=1[NH2:13]

Participants

4

Reactant 2

HCID 21124087PyridiniumtribromideHCID 686567951-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine

Product 1

HCID 686571164-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-(2,2-Dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (3.52 g, 17.2 mmol, 1.0 equiv.) was dissolved in chloroform (172 ml) and treated with pyridinium tribromide (5.51 g, 17.2 mmol, 1.0 equiv.). The mixture was stirred at room temperature until LCMS showed almost only product. The solid was collected on top of filter and washed with hexanes. The solid was dissolved in Et2O/EtOAc and neutralized with saturated aqueous sodium bicarbonate. The organic layers were separated, dried with magnesium sulfate, filtered and concentrated in vacuo to provide the titled compound as a pale white solid: 1H NMR (500 MHz, CD3OD) 7.30 (d, 1H, J=8.8 Hz), 7.07 (sb, 3H), 7.02 (d, 1H, J=8.8 Hz), 4.34 (s, 2H), 1.03 (s, 9H) ppm. LRMS m/z (M+H) 283.0 and 285.0 (intensity ratio ˜1:1) found, 283.1 and 285.1 required.

Workup

  1. customThe solid was collected on top
  2. filtrationof filter
  3. washwashed with hexanes
  4. dissolutionThe solid was dissolved in Et2O/EtOAc and neutralized with saturated aqueous sodium bicarbonate
  5. customThe organic layers were separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e3c1b8c11d44aa18ecb71fe21258a79
Source dataset
uspto-grants-2014_07
Patent number
US08772276B2

Reaction notes

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