Sodium Chloride → Diethyl [1-(4-acetamidophenyl)-1-oxopropan-2-yl]propanedioate

HRID 1766188Notes

Reaction equation

HRID 1766188 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:28])[CH:25](Cl)[CH3:26])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].[Cl-].[Na+].[K+].[Br-]>CN(C)C=O>[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:28])[CH:25]([CH3:26])[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 253877Potassium BromideHCID 322933N-[4-(2-chloropropanoyl)phenyl]acetamide

Product 1

HCID 13052563Diethyl [1-(4-acetamidophenyl)-1-oxopropan-2-yl]propanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

24.407 ml. (0.16 mol) of diethyl malonate were added dropwise to a suspension of 7.631 g (0.159 mol) of sodium hydride in 90 ml of anhydrous dimethylformamide under a nitrogen atmosphere, the mixture was heated for 90 minutes to 50° C., then 37.462 g (0.166 mol) of 1-(4-acetylaminophenyl)-2-chloro-1-propanone were added and heating was continued for a further 3 hours to 80° C. After cooling the mixture was stirred into 1 l of ice water, saturated with sodium chloride and extracted exhaustively with ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulphate, filtered over activated charcoal and concentrated by evaporation in vacuo, and the residue was purified by column chromatography on silica gel. After working up in the usual way 45.0 g (80% of theoretical) of a colourless oil were obtained, Rf 0.7 (El: EE). IR (KBr): 1747, 1732, 1676 cm−1 (C═O) MS: M+349

Workup

  1. temperaturethe mixture was heated for 90 minutes to 50° C.
  2. temperatureheating
  3. temperatureAfter cooling the mixture
  4. extractionextracted exhaustively with ethyl acetate
  5. dry with materialThe combined ethyl acetate extracts were dried over sodium sulphate
  6. filtrationfiltered over activated charcoal
  7. concentrationconcentrated by evaporation in vacuo
  8. customthe residue was purified by column chromatography on silica gel
  9. customwere obtained

Sources & evidence

ORD record
ord-4d6997c6791647458978067ac5aee637
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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