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

HRID 1432846

Reaktionsgleichung

Reaktionsgleichung von HRID 1432846
[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

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 79323-ChloroanilineHCID 230201alpha-Methylcinnamoylchloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d75b3cf4cbe34783ac2c494fa33f0625
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612075B2

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