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

HRID 2281055Notes

Reaction equation

HRID 2281055 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, 17.23 mmol, 1.0 equiv.) was dissolved in chloroform (172 ml) and treated with pyridinium tribromide (5.51 g, 17.23 mmol, 1.0 equiv.). The mixture was stirred at room temperature until LCMS showed almost only product was observed. The mixture was filtered and the solid was washed with hexane, which was dissolved in diethyl ether/ethyl acetate and neutralized with saturated aqueous sodium bicarbonate. The organic extracts were dried with magnesium sulfate, filtered and concentrated in vacuo, providing 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. filtrationThe mixture was filtered
  2. washthe solid was washed with hexane, which
  3. dissolutionwas dissolved in diethyl ether/ethyl acetate and neutralized with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21e8d356ccfb4d499271320c3ccea7e4
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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