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

HRID 1626995Notes

Reaction equation

HRID 1626995 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 indicated the reaction was complete. The mixture was filtered, the solid was collected and washed with hexanes. The solid was dissolved in diethyl ether/ethyl acetate and treated with saturated aqueous sodium bicarbonate. The organic layers was separated, dried with magnesium sulfate, filtered and concentrated in vacuo, providing the titled compound as pale white solid: 1H NMR (500 MHz, CD3OD) 7.30 (d, 1H, J=8.8 Hz), 7.07 (br s, 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. customthe solid was collected
  3. washwashed with hexanes
  4. dissolutionThe solid was dissolved in diethyl ether/ethyl acetate
  5. additiontreated with saturated aqueous sodium bicarbonate
  6. customThe organic layers was separated
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c62882422524d8f932ee8d73aa231e5
Source dataset
uspto-grants-2014_07
Patent number
US08785482B2

Reaction notes

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