Dimethylformamide → HCID 69209009, compound

HRID 30659

Reaction equation

HRID 30659 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:15][C:16](=O)[CH2:17][CH3:18].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH2:17]([C:16]1[N:13]=[C:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[O:12][CH:15]=1)[CH3:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 131561-Bromo-2-butanoneHCID 2336132-(4-Nitrophenyl)acetamide

Product 1

HCID 69209009HCID 69209009, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-(4-nitrophenyl)acetamide (14.6 g), 1-bromo-2-butanone (20.46 g) and N,N-dimethylformamide (2 mL) was stirred at 140° C. for 2 hrs. Water, potassium carbonate and ethyl acetate were added to basify 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 4-ethyl-2-(4-nitrobenzyl)-1,3-oxazole as brown crystals (2.65 g, yield 14%) from a fraction eluted with hexane-ethyl acetate (2:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave brown prism crystals. melting point: 58-59° 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-b56ec8bd870e48eab7445f993a260e0a
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

Loading…