Sodium Azide → 2-(Azidomethyl)-5-methyl-1,3,4-oxadiazole

HRID 1365749Notes

Reaction equation

HRID 1365749 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]([CH3:8])=[N:6][N:7]=1.[N-:9]=[N+:10]=[N-:11].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:9]([CH2:2][C:3]1[O:4][C:5]([CH3:8])=[N:6][N:7]=1)=[N+:10]=[N-:11]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazole

Product 1

HCID 596467682-(Azidomethyl)-5-methyl-1,3,4-oxadiazoleYield 84.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(chloromethyl)-5-methyl-1,3,4-oxadiazole (R. Rufenacht, Helv. Chim. Acta, 55, 1979, 1972) (2.00 g, 15.09 mmol) in N,N-dimethylformamide (75 ml) was treated at 22° C. with sodium azide (3.0 g, 46.1 mmol) and the resulting mixture was stirred for 18 h. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure followed by chromatography of the residue on silica gel (elution toluene-ethyl acetate 0-10%) gave 1.78 g (84% yield) of the title azide as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.60 (3H, s, CH3), 4.55 (2H, s, CH2). MS (ESI+) m/e 140 [M+H+].

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-d9468f3c1a13477e9eac5da7d896a048
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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