Sodium Azide → 3-(Azidomethyl)-5-methyl-1,2-oxazole

HRID 2111679Notes

Reaction equation

HRID 2111679 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[N-:9]=[N+:10]=[N-:11].[Na+]>CN(C=O)C.O>[N:9]([CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1)=[N+:10]=[N-:11]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazole

Product 1

HCID 234409373-(Azidomethyl)-5-methyl-1,2-oxazoleYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Chloromethyl-5-methylisoxazole (500 mg, 3.8 mmol) and sodium azide (494 mg, 7.6 mmol) were heated in DMF (10 ml) at 60° C. for 6 hours. The reaction mixture was diluted with water then extracted with EtOAc. The organic extracts were dried (MgSO4) and the volatiles removed by evaporation to give the title compound (387 mg, 73%) as an oil. NMR (DMSO): 2.40 (s, 3H), 4.48 (s, 2H), 6.28 (s, 1H).

Workup

  1. extractionthen extracted with EtOAc
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-54ceae5d828b4fef9058789fa5954f32
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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