Sodium Azide → (+/-)-1-Methoxy-2-butyl Azide

HRID 1279270Notes

Reaction equation

HRID 1279270 reaction equation
CS(O[CH:6]([CH2:10][CH3:11])[CH2:7][O:8][CH3:9])(=O)=O.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[CH3:9][O:8][CH2:7][CH:6]([N:12]=[N+:13]=[N-:14])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22273165(+/-)-1-Methoxy-2-butanol Methanesulfonate

Product 1

HCID 18689797(+/-)-1-Methoxy-2-butyl Azide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

A solution of crude mesylate 1 (90.0 g, 0.495 mol) in DMF (500 mL) was treated with NaN3 (48.22g, 0.74 mol, 1.5 equiv) at 25° C. under N2. The resulting reaction mixture was warmed to 55-60° C. for 6-8 h with stirring before being quenched with H2O (500 mL). The pale-yellow solution was then extracted with EtOAc or Et2O (4×200 mL). The combined EtOAc (or Et2O) extracts were washed with H2O (3×500 mL), dried (MgSO4), and concentrated in vacuo. The residual solution was found to contain desired azide 2 (60.3 g, 64.5 g theoretical, 94%), which was found to be pure enough and directly used in the following reaction without further purification.

Workup

  1. customThe resulting reaction mixture
  2. custombefore being quenched with H2O (500 mL)
  3. extractionThe pale-yellow solution was then extracted with EtOAc or Et2O (4×200 mL)
  4. washThe combined EtOAc (or Et2O) extracts were washed with H2O (3×500 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customdirectly used in the following reaction without further purification

Sources & evidence

ORD record
ord-f134f37cef8549998671f490a3d8fda0
Source dataset
uspto-grants-2002_09
Patent number
US06448261B1

Reaction notes

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