Triethylamine → 3-chloro-N-(3-fluorophenyl)propanamide

HRID 1521637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521637
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(N(CC)CC)C.[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>ClCCl.O>[Cl:16][CH2:17][CH2:18][C:19]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([F:1])[CH:3]=1)=[O:20]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 97423-FluoroanilineHCID 693643-Chloropropionyl chloride

Produkt 1

HCID 35556953-chloro-N-(3-fluorophenyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 3-fluoroaniline (20 g, 0.180 mol) in dichloromethane (100 mL) was added triethylamine (21.816 g, 0.216 mol) and 3-chloropropanoyl chloride (17.18 mL, 0.180 mol) under cooling condition (0° C.) with constant stirring. Reaction mass was allowed to stir at room temperature for 12 h. The reaction mixture was diluted with water (300 mL) and extracted with dichloromethane (4×100 mL). The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 7.51-7.48 (d, J=10.4 Hz, 1H), 7.42 (bs, 1H), 7.29-7.24 (dd, J=14.8 Hz, 8.0 Hz, 1H), 7.15-7.13 (d, J=8.0 Hz, 1H), 6.84-6.81 (t, J=6.8 Hz, 1H), 3.89-3.86 (t, J=6.4 Hz, 2H), 2.83-2.80 (t, J=6.4 Hz, 2H). MS (M+1): 201.9.

Aufarbeitung

  1. customReaction mass
  2. extractionextracted with dichloromethane (4×100 mL)
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b8a90603582e4bbf9ad7dbb5e9516811
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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