Ethanol → HCID 22170378, compound

HRID 1822868Notes

Reaction equation

HRID 1822868 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[N-:13]=[N+:14]=[N-:15].[Na+].C(O)C>O>[CH3:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][N:13]=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 33557Sodium AzideHCID 108947alpha-Chloro-2-methyl-3-nitrotoluene

Product 1

HCID 22170378HCID 22170378, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2-methyl-3-nitrobenzylchloride (0.70 g, 3.77 mmol), sodium azid (1 g, 15.4 mmol), ethanol (10 ml) and water (2 ml) was heated at 45° C. over night. The mixture was filtered, the filtrate was concentrated, and the residue was purified by chromatography on silica (heptane/EtOAc) to give the compound 2-methyl-3-nitrobenzylazide 0.35 g, which was hydrogenated over 5% palladium-charcoal 80 mg in EtOAc/EtOH 1:1 (14 ml), over night. The mixture was filtered through Celite, and the filtrated was concentrated to give 0.23 g (45%) of the title compound as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by chromatography on silica (heptane/EtOAc)

Sources & evidence

ORD record
ord-43472d6beb6c4cbbbfbdccb7ce2cfc9b
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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