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

HRID 566142Notes

Reaction equation

HRID 566142 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-82282fdc39894edf862abf3428fcaaf4
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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