Ammonium Chloride → 1-Azido-3,3-dimethylbutan-2-ol

HRID 601623

Reaction equation

HRID 601623 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[CH3:7][C:8]([CH3:13])([CH3:12])[CH:9]1[O:11][CH2:10]1>CO.O>[N:1]([CH2:10][CH:9]([OH:11])[C:8]([CH3:13])([CH3:12])[CH3:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 921742-tert-Butyloxirane

Product 1

HCID 146113101-Azido-3,3-dimethylbutan-2-olYield 94%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Sodium azide (10 g, 154 mmol) and ammonium chloride (3.7 g, 070 mmol) are added to a solution of 3,3-dimethyl-1,2-epoxybutane (4.26 ml, 35 mmol) in methanol:water (8:1, 315 ml), and the mixture is heated at reflux for 7 hours. The reaction is poured into ice/water (400 ml) and extracted with dichloromethane (3×200 ml). The combined organics are dried (MgSO4), filtered and evaporated to yield a clear oil (4.7 g, 94 %).

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 7 hours
  3. extractionextracted with dichloromethane (3×200 ml)
  4. dry with materialThe combined organics are dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1606f288f1394d7383b142d373e1f0d7
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Linked notes

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