4-Chloro-3-methylaniline → N-(4-Chloro-3-methylphenyl)cinnamamide

HRID 1045367

Reaktionsgleichung

Reaktionsgleichung von HRID 1045367
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[C:10](Cl)(=[O:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:10](=[O:19])[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:3]=1[CH3:9]

Komponenten

5

Edukt 2

HCID 235364-Chloro-3-methylanilineHCID 660233-Phenylprop-2-enoyl chloride

Produkt 1

HCID 66911299N-(4-Chloro-3-methylphenyl)cinnamamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 4-chloro-3-methylaniline (3.33 g, 19.98 mmole) in dichloromethane (100 mL) and pyridine (20 mL) was added cinnamoyl chloride (2.83 g, 19.98 mmole) at 0° C. The mixture was stirred at room temperature for 2 h. Solvent and pyridine were removed by rotary evaporator under reduced pressure. The residue was diluted with ethyl acetate and washed 1N HCl (2×100 mL), water (2×100 mL), sodium bicarbonate solution (2×100 mL) and dried over sodium sulfate. After removing solvent a white solid was recovered (5.38 g, 99% yield). The product was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 7.76-7.24 (m, 10H), 6.58 (d, 1H), 2.55 (s, 3H); MS (ESI) m/z: Calculated for C16H14ClNO: 271.1. found: 272 (M+H)+.

Aufarbeitung

  1. customSolvent and pyridine were removed by rotary evaporator under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed 1N HCl (2×100 mL), water (2×100 mL), sodium bicarbonate solution (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customAfter removing solvent a white solid
  6. customwas recovered (5.38 g, 99% yield)
  7. customThe product was used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ad3c2e35a60540d8978dd9156aa58dc3
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569282B2

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