2-Chloroethyl isocyanate → 1-(2-Chloro-ethyl)-3-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionyl]-urea

HRID 1860176노트

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HRID 1860176 반응식
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:19][CH2:20][CH2:21][N:22]=[C:23]=[O:24]>C1(C)C=CC=CC=1>[Cl:19][CH2:20][CH2:21][NH:22][C:23]([NH:10][C:8](=[O:9])[CH:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:24]

참가 물질

4

반응물 2

HCID 160352-Chloroethyl isocyanateHCID 186266403-Cyclopentyl-2-(3,4-dichloro-phenyl)-propionamide

생성물 1

HCID 99085001-(2-Chloro-ethyl)-3-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionyl]-urea수율 76%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
25 °C

실험 절차

A solution of 3-cyclopentyl-2-(3,4-dichloro-phenyl)-propionamide (prepared in Example 12, 182 mg, 0.64 mmol) in toluene (10 mL) was treated with 2-chloroethyl isocyanate (0.08 mL, 0.95 mmol). The reaction was heated at reflux for 16 h. At this time, the reaction was cooled to 25° C. and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/10 hexanes/ethyl acetate) afforded 1-(2-chloro-ethyl)-3-[3-cyclopentyl-2-(3,4-dichlorophenyl)-propionyl]-urea (189 mg, 76%) as a colorless oil: EI-HRMS m/e calcd for C17H21Cl3N2O2 (M+) 390.0669, found 390.0659.

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b62ae1a3314148ccb03a5c719bd6a5a9
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06528543B1

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