Triethylamine → N-(3-cyclopentyloxy-4-methoxyphenyl)-2,6-dichlorobenzamide

HRID 356901

Reaktionsgleichung

Reaktionsgleichung von HRID 356901
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[NH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26](Cl)=[O:27]>ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([NH:10][C:26](=[O:27])[C:25]3[C:24]([Cl:23])=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:33])[CH:11]=[CH:12][C:13]=2[O:14][CH3:15])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 783922,6-Dichlorobenzoyl chlorideHCID 27793343-(Cyclopentyloxy)-4-methoxyaniline

Produkt 1

HCID 21187908N-(3-cyclopentyloxy-4-methoxyphenyl)-2,6-dichlorobenzamideAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of 3-cyclopentyloxy-4-methoxyaniline (1 g) and triethylamine (0.69 mL) in dry dichloromethane (20 mL) at 0° C. is treated dropwise with 2,6-dichlorobenzoyl chloride (1.17 g). After stirring at this temperature for 30 minutes, the mixture is warmed to room temperature and stirred for a further 3 hours. The organic layer is washed with water (100 mL), dried and concentrated. The residue is recrystallized from a mixture of isopropanol and hexane, to give N-(3-cyclopentyloxy-4-methoxyphenyl)-2,6-dichlorobenzamide (0.6 g), m.p. 184°-185° C. [Elemental analysis: C,60.2,H,5.0; N,3.6; Cl18.9%; calculated: C,60.0; H,5.0; N,3.7; Cl18.65%].

Aufarbeitung

  1. stirringstirred for a further 3 hours
  2. washThe organic layer is washed with water (100 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is recrystallized from a mixture of isopropanol and hexane

Quellen und Nachweise

ORD-Eintrag
ord-2e58363523284db9afa04a2261945613
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840724

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