Dimethylformamide → 3-ethyl-5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one

HRID 30669Notes

Reaction equation

HRID 30669 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][C:9]2[O:13][C:12](=[O:14])[NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].I[CH2:18][CH3:19].CN(C)C=O.[H-].[Na+]>O>[CH2:18]([N:11]1[N:10]=[C:9]([CH2:8][C:7]2[CH:15]=[CH:16][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[O:13][C:12]1=[O:14])[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 218227135-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 692102783-ethyl-5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one (1.50 g), iodoethane (1.59 g) and N,N-dimethylformamide (50 mL) was added sodium hydride (60% in oil, 0.30 g) at room temperature. The reaction mixture was stirred at room temperature for 3 hrs. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 3-ethyl-5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one as colorless crystals (0.99 g, yield 59%) from a fraction eluted with hexane-ethyl acetate (3:1-2:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 108-109° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2ca7066f5bf64d87b6f2cbd46462b3bb
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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