Hydrochloric Acid → N-(3-Chloro-2-fluoro-benzyl)-acrylamide

HRID 1527353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527353
[F:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].Cl>C1COCC1.CCOC(C)=O>[Cl:10][C:9]1[C:2]([F:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH2:4][NH:5][C:11](=[O:14])[CH:12]=[CH2:13]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 2773614(3-Chloro-2-fluorophenyl)methanamine

Produkt 1

HCID 68283248N-(3-Chloro-2-fluoro-benzyl)-acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of 2-fluoro-3-chlorobenzylamine (1 g, 6.27 mmol) and TEA (1.05 mL, 7.52 mmol) in THF (20.9 mL) was added acryloyl chloride (0.61 mL, 7.52 mmol) dropwise and the reaction mixture was stirred at 23° C. for 2 h. The reaction mixture was diluted in EtOAc, HCl 1N was added and the layers separated. The aqueous layer was extracted again with EtOAc and the combined organic layers were dried, filtered and concentrated to dryness. The crude residue was purified by flash column chromatography on silica gel (xyclohexane/EtOAc gradient 100:0 to 1:1) to give the desired material. TLC, Rf (c-hexane/EtOAc 5:5)=0.41; MS (LC/MS): 214.0 [M+H]+; tR (HPLC conditions b): 3.35 min.

Aufarbeitung

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted again with EtOAc
  3. customthe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude residue was purified by flash column chromatography on silica gel (xyclohexane/EtOAc gradient 100:0 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ac1823669f5549fba2051c1fe29970e3
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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