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

HRID 1432846ノート

反応式

HRID 1432846 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 79323-ChloroanilineHCID 230201alpha-Methylcinnamoylchloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-d75b3cf4cbe34783ac2c494fa33f0625
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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