Water → HCID 66676906, compound

HRID 423285Notes

Reaction equation

HRID 423285 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[CH:6]=[C:7]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C=O)C>[CH2:27]([O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:7]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:5]([C:3](=[O:4])[N:2]([CH3:1])[CH3:20])[CH:6]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66677056HCID 66677056, compound

Product 1

HCID 66676906HCID 66676906, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(3-dimethylcarbamoyl-4-nitrophenyl)butanoic acid (1.37 g) in DMF (10 mL) were added potassium carbonate (880 mg) and benzyl bromide (922 mg). The mixture was stirred at 60° C. for 3.5 hours under heating and then allowed to stand for cooling down to room temperature. After addition of water thereto, the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1, v/v) to give the title compound (1.39 g).

Workup

  1. temperatureunder heating
  2. temperaturefor cooling down to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-e230019f5e5b4d169920f76045cb2247
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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