Sodium Azide → Azidomethyl 2,2-dimethylpropanoate

HRID 385971Notes

Reaction equation

HRID 385971 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

Conditions

Temperature
90 °C

Procedure

Chloromethyl pivalate (1.93 ml, 12.9 mmol) and sodium azide (1.27 g, 19.3 mmol) were taken up in water (52 ml). The reaction mixture was heated to 90° C. for 22 hours. The reaction mixture was cooled to ambient temperature, and extracted with ethyl acetate three times. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate three times
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15529bdcea904d63961c709190d9b360
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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