Ethyl chloroacetate → 3-(3-Benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile

HRID 600822노트

반응식

HRID 600822 반응식
[CH2:1]([NH:8][C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][C:13]=1[NH:20][CH2:21][CH3:22])=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:24][C:25](OCC)=[O:26].C1CCN2C(=NCCC2)CC1>C(O)C>[CH2:1]([N:8]1[C:25](=[O:26])[CH2:24][S:10][C:9]1=[N:11][C:12]1[CH:17]=[C:16]([CH:15]=[CH:14][C:13]=1[NH:20][CH2:21][CH3:22])[C:18]#[N:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7751Ethyl chloroacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219373781-Benzyl-3-(5-cyano-2-ethylaminophenyl)thiourea

생성물 1

HCID 219373763-(3-Benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile수율 87.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

To a solution of 1-benzyl-3-(5-cyano-2-ethylaminophenyl)thiourea (1.0 g, 3.2 mmol) in ethanol (40 mL, anhyd) was added ethyl chloroacetate (0.39 g, 3.2 mmol) and then DBU (0.58 g, 3.8 mmol). The reaction mixture was heated at 80° C. with stirring. After 1 h the reaction mixture was cooled, concentrated under reduced pressure, and chromatographed (silica gel, 1:1 EtOAc/Hex) to afford the title product (0.98 g, 87%). 1H-NMR (CDCl3): δ 7.38 (6H, m), 7.11 (1H, d), 6.50 (1H, d), 5.05 (2H, s), 3.96 (2H, s), 3.01 (2K, m), 1.03 (3H, t).

후처리

  1. temperatureAfter 1 h the reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customchromatographed (silica gel, 1:1 EtOAc/Hex)

출처 및 근거

ORD 기록
ord-c6e19151a97d482c852c0612aa887304
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902237B2

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