3-Chloro-4-fluoroaniline → 2-(3-Chloro-4-fluorophenylamino)-N-(5-methoxy-2-methylphenyl)-acetamide

HRID 1267922

Reaktionsgleichung

Reaktionsgleichung von HRID 1267922
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[CH3:14])=[O:4].[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[F:23])[NH2:19].C(N(C(C)C)CC)(C)C>[I-].[K+].O1CCCC1>[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][CH2:2][C:3]([NH:5][C:6]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=2[CH3:14])=[O:4])[CH:20]=[CH:21][C:22]=1[F:23]

Komponenten

6

Edukt 3

HCID 97083-Chloro-4-fluoroanilineHCID 81531DiisopropylethylamineHCID 11328892-chloro-N-(5-methoxy-2-methylphenyl)acetamide

Produkt 1

HCID 185424132-(3-Chloro-4-fluorophenylamino)-N-(5-methoxy-2-methylphenyl)-acetamideAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Chloro-N-(5-methoxy-2-methylphenyl)-acetamide (3 g), 3-chloro4-fluoroaniline (7.56 g), diisopropylethylamine (13.8 ml), potassium iodide (0.005 g) and anhydrous tetrahydrofuran (20 ml) were heated together at 105° C. in a sealed tube for 19 hours. The mixture was then cooled and concentrated. Purification of the residue by silica gel chromatography (eluting with 1:1 iso-hexane/ethyl acetate) gave the sub-title compound (3.93 g).

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated
  3. customPurification of the residue
  4. washby silica gel chromatography (eluting with 1:1 iso-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5f5bdb6f7f7342ad9881942083b51512
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555541B1

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