Water → Propanoic acid, 3-oxo-3-(phenylamino)-, ethyl ester

HRID 658355Notes

Reaction equation

HRID 658355 reaction equation
C([CH:3]([C:7](Cl)=[O:8])[C:4](Cl)=[O:5])C.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N([CH2:22][CH3:23])CC)C.ClCCl.[OH2:27]>>[CH2:22]([O:27][C:7](=[O:8])[CH2:3][C:4](=[O:5])[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:23]

Participants

6

Reactant 5

HCID 962WaterHCID 6115AnilineHCID 6344DichloromethaneHCID 8471TriethylamineHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 3016808Propanoic acid, 3-oxo-3-(phenylamino)-, ethyl esterYield 94%

Procedure

Ethyl malonyl chloride (15.1 g, 0.10 mol) was added to a mixed solution of aniline (9.3 g, 0.10 mol), triethylamine (11.1 g, 0.11 mol), N,N-dimethylaminopyridine (1.5 g, 0.012 mol) and dichloromethane (300 mL), at 10° C. or below. This mixture was stirred for 3 hours at room temperature, and then poured into water. The organic layer was washed with diluted hydrochloric acid, aqueous saturated sodium bicarbonate and saturated brine, in this order. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to obtain 19.5 g of a subject compound (yield: 94%).

Workup

  1. washThe organic layer was washed with diluted hydrochloric acid, aqueous saturated sodium bicarbonate and saturated brine, in this order
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b7f0899d3d3144899c4f98dfa32e8ab7
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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