Sodium Azide → Azidomethyl 2,2-dimethylpropanoate

HRID 1480439Notes

Reaction equation

HRID 1480439 reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N-:10]=[N+:11]=[N-:12].[Na+]>O>[C:1]([O:7][CH2:8][N:10]=[N+:11]=[N-:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 87885Chloromethyl pivalate

Product 1

HCID 11521126Azidomethyl 2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of chloromethyl pivalate (21.2 g, 141 mmol) in water (25 ml) was added sodium azide (13.7 g, 211 mmol) and the mixture was stirred vigorously at 90° C. for 24 hrs. On cooling the reaction mixture was diluted with H2O and the organic portion was filtered through a pad of MgSO4 to afford the title compound as a clear liquid;

Workup

  1. temperatureOn cooling the reaction mixture
  2. filtrationthe organic portion was filtered through a pad of MgSO4

Sources & evidence

ORD record
ord-e843f371d66d4eaa9faa6240a43265a7
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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