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

HRID 1449508Notes

Reaction equation

HRID 1449508 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-:5])=O.[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>ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]([NH:14][C:3]([CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[O:5])[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-oxopropanoateYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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

Workup

  1. temperatureUnder cooling with ice, to the solution
  2. customInsoluble materials was 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

Sources & evidence

ORD record
ord-e8421f2757c04ce7bf8fb09fa97857a5
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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