4-Chloroaniline → Ethyl 3-[(4-chlorophenyl)amino]-3-oxopropanoate

HRID 2104409노트

반응식

HRID 2104409 반응식
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([O-])=[O:12].[K+].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH2:16]([O:15][C:9](=[O:14])[CH2:10][C:11]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:12])[CH3:17]

참가 물질

7

반응물 4

HCID 78124-ChloroanilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3446434Potassium ethyl malonate

생성물 1

HCID 1518288Ethyl 3-[(4-chlorophenyl)amino]-3-oxopropanoate수율 105.6%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-chloroaniline (2.0 g) in N,N-dimethylformamide (20 mL) were sequentially added at room temperature potassium ethyl malonate (3.2 g), 1-hydroxybenzotriazole (2.1 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.5 g), followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogencarbonate, 10% aqueous citric acid, and saturated brine. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure, to thereby give the title compound (4.0 g).

후처리

  1. washwashed with saturated aqueous sodium hydrogencarbonate, 10% aqueous citric acid, and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. distillationthe solvent was distilled away under reduced pressure

출처 및 근거

ORD 기록
ord-344dad770ea44432896190fb46a54b74
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576135B2

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