Pyridine → N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamide

HRID 1432846노트

반응식

HRID 1432846 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[CH3:15][C:16](=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17](Cl)=[O:18]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:17](=[O:18])[C:16]([CH3:15])=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 79323-ChloroanilineHCID 230201alpha-Methylcinnamoylchloride

생성물 1

HCID 3497717N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 3-chloroaniline (0.98 mL, 9.3 mmol) in CH2Cl2 (25 mL) at 0° C. is added pyridine (0.78 mL, 9.5 mmol). To the resulting solution is added dropwise a solution of α-methyl cinnamic acid chloride (1.6 g, 9.3 mmol) in CH2Cl2 (8 mL). After 3 hours, the solution is concentrated. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound is obtained as a solid (2.5 g, 9.2 mmol). 1H NMR (CDCl3, 300 MHz) δ7.95 (m, 1H), 7.73 (s, 1H), 7.46 (m, 1H), 7.33 (m, 6H), 7.22 (m, 1H), 7.03 (m, 1H), 2.13 (s, 3H).

후처리

  1. concentrationthe solution is concentrated
  2. customThe crude product is purified by column chromatography
  3. washeluting with 5% EtOAc/hexanes to 10% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-d75b3cf4cbe34783ac2c494fa33f0625
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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