Water → HCID 86647413, compound

HRID 2070945Notes

Reaction equation

HRID 2070945 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]([CH3:12])=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1.[N-:14]=[N+:15]=[N-:16].[Na+].O.CCOC(C)=O>CN(C=O)C>[N:14]([CH2:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]([CH3:12])=[C:7]([C:9]([CH3:11])=[CH2:10])[CH:8]=1)=[N+:15]=[N-:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 68670764HCID 68670764, compound

Product 1

HCID 86647413HCID 86647413, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 96.5 mg of the 3-(chloromethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)pyridine and 86.8 mg (1.34 mmol) of NaN3 in 3 mL of DMF was heated at 70° C. for 4 h. Water and EtOAc were added, and the layers were separated. The organic layer was washed with H2O (2×) and then with brine. It was dried over Na2SO4, filtered, and concentrated to give the crude azide (3-(azidomethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)pyridine) which was used without further purification.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with H2O (2×)
  3. dry with materialIt was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-435f5a11b9c54a84ae187c5b90f43d93
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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