Triethylamine → N-(2,4-Dichlorophenyl)-3-(phenylmethoxy)benzeneacetamide

HRID 2114735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114735
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]1([CH2:16][O:17][C:18]2[CH:19]=[C:20]([CH2:24][C:25](Cl)=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:25](=[O:26])[CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH2:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:19]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 111232,4-DichloroanilineHCID 516892Sodium BicarbonateHCID 118178352-[3-(Phenylmethoxy)phenyl]acetyl Chloride

Produkt 1

HCID 23440745N-(2,4-Dichlorophenyl)-3-(phenylmethoxy)benzeneacetamideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2,4-dichloroaniline (2.67 g, 0.0165 mol) in dichloromethane (20 ml) was slowly added a solution of 2-[3-(phenylmethoxy)phenyl]acetyl chloride (3.84 g, 0.015 mol) in dichloromethane (10 ml). After stirring for three hours, triethylamine (2 ml, 0.015 mol) was added to the reaction and the reaction was allowed to stir overnight. To the reaction was added an aqueous solution of sodium bicarbonate. The mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The solid was triturated with ether and hexane, then filtered to provide the title compound (4.0 g, 70% yield): ES-MS (m/z) 372 [M+H]+.

Aufarbeitung

  1. stirringto stir overnight
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solid was triturated with ether and hexane
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-e9302f6c18044f1e991ea721585fa783
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435729B2

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