Pyridiniumtribromide → HCID 67606434, compound

HRID 1626970Notes

Reaction equation

HRID 1626970 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.[Br-:16].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(O)(=O)C>[Br:16][C:13]1[C:8]2[N:7]=[N:6][N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:9]=2[CH:10]=[CH:11][C:12]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 21124087PyridiniumtribromideHCID 686570341-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole

Product 1

HCID 67606434HCID 67606434, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole (22.0 g, 108 mmol) was dissolved in acetic acid (250 ml) and treated with pyridinium tribromide (41.5 g, 130 mmol). After stirring for 14 hours, the mixture was concentrated to the minimum amount of solvent with stirring volume. The residue was dissolved in ethyl acetate and washed with 1 N aqueous NaOH and diluted in an equal volume of water. The organic layer was removed, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (10 to 50% ethyl acetate in heptane), providing the titled compound as an orange solid.

Workup

  1. concentrationthe mixture was concentrated to the minimum amount of solvent
  2. stirringwith stirring volume
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1 N aqueous NaOH
  5. additiondiluted in an equal volume of water
  6. customThe organic layer was removed
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (10 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b6ef1ca3e5644ae38af20ca6f649552e
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

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