Dicyclohexylcarbodiimide → Ethyl 3-[(3,5-dichlorophenyl)amino]-3-oxopropanoate

HRID 1449528Notes

Reaction equation

HRID 1449528 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([O-:8])=O)[CH3:2].[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[NH2:14].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([NH:14][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:9])=[O:8])[CH:15]=[C:16]([Cl:18])[CH:17]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 122813,5-DichloroanilineHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 17097472Ethyl 3-[(3,5-dichlorophenyl)amino]-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 200 ml of methylene chloride were dissolved 5.0 g of monoethylmalonate and 6.12 g of 3,5-dichloroaniline. Under cooling with ice, to the mixture was added 8.57 of N,N'-dicyclohexylcarbodiimide, followed by stirring at room temperature for 5 hours. Insoluble materials were removed by filtration. The filtrate was diluted with ethyl acetate, washed with 1N hydrochloric acid and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (silica gel:250 g) using a mixed solvent of chloroform and acetone (20:1 by volume) to obtain 6.57 g of the oily titled comouond.

Workup

  1. temperatureUnder cooling with ice, to the mixture
  2. customInsoluble materials were removed by filtration
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with 1N hydrochloric acid
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residue was purified by silica gel column chromatography (silica gel:250 g)
  7. customto obtain 6.57 g of the oily titled comouond

Sources & evidence

ORD record
ord-a7144ac08c5045ce8061f09865980f75
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

Loading…