Dimethylformamide → ethyl 4-(4-bromo-2,N-diformylanilino)butyrate

HRID 1388070Notes

Reaction equation

HRID 1388070 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[O:10])=[C:4]([CH:11]=[O:12])[CH:3]=1.Br[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]=[O:10])=[C:4]([CH:11]=[O:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 570527524-Bromo-2-formylphenylformamide

Product 1

HCID 21715711ethyl 4-(4-bromo-2,N-diformylanilino)butyrateYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 4-bromo-2-formylphenylformamide (18.07 g), ethyl 4-bromobutyrate (30.9 g) and potassium carbonate (21.9 g) was added DMF (160 ml), and the mixture was stirred at 70° C. for 24 hours. The mixture was dilute with ethyl acetate (1400 ml), washed with water (300 ml×3) and saturated brine (150 ml), and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (300 g, hexane:ethyl acetate=4:1→1:1) to give ethyl 4-(4-bromo-2,N-diformylanilino)butyrate (21.56 g, 80%).

Workup

  1. washwashed with water (300 ml×3) and saturated brine (150 ml)
  2. dry with materialdried with magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified with silica gel column chromatography (300 g, hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-b09872e8bfe7477d8f4be40ecb700a83
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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