Sodium Carbonate → N-(4-Bromo-2,6-dichloro-phenyl)-2-cyclopentyl-acetamide

HRID 1820114

Reaktionsgleichung

Reaktionsgleichung von HRID 1820114
[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5]([NH2:6])=[C:4]([Cl:10])[CH:3]=1.[CH:11]1([CH2:16][C:17](Cl)=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5]([NH:6][C:17](=[O:18])[CH2:16][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([Cl:10])[CH:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 696804-Bromo-2,6-dichloroanilineHCID 3485182Cyclopentylacetyl chloride

Produkt 1

HCID 68711978N-(4-Bromo-2,6-dichloro-phenyl)-2-cyclopentyl-acetamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Bromo-2,6-dichloroaniline (12.1 g) and cyclopentylacetyl chloride (8.1 g) were dissolved in tetrahydrofuran (100 mL) and sodiumcarbonate (6.4 g) is added, followed by heating to reflux for 6 hours. The reaction mixture was cooled to ambient temperature and filtered and diluted with water (250 ml). After extraction, the combined organic phase was concentrated in vacuo to furnish 14.0 g (80% yield) of the title compound as a white solid. LC-MS (m/z) 352 (MH+); tR=3.47, (UV, ELSD) 96%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.12 (m, 2H), 1.50 (m, 4H), 1.80 (m, 2H), 2.15 (m, 1H), 2.50 (d, 2H), 5.70 (broad s, 1H), 7.45 (s, 2H).

Aufarbeitung

  1. temperatureby heating
  2. temperatureto reflux for 6 hours
  3. filtrationfiltered
  4. additiondiluted with water (250 ml)
  5. extractionAfter extraction
  6. concentrationthe combined organic phase was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-97f69c1dc8f144b8a7615fd4c1f61766
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601870B2

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