4-Chloroaniline → 2-amino-N-(4-chlorophenyl)benzamide

HRID 2300914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2300914
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[O:9]1[CH2:14][CH2:13]OCC1>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:9])[C:13]2[CH:8]=[CH:2][CH:3]=[CH:4][C:5]=2[NH2:6])=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 78124-ChloroanilineHCID 312751,4-Dioxane

Produkt 1

HCID 6704722-amino-N-(4-chlorophenyl)benzamide

Versuchsvorschrift

A mixture of benzoxazine-2,4-dione (1.6 g, 10 mmol) and 4-chloroaniline (2.5 g, 20 mmol) in 1,4-dioxane (30 mL) was heated at reflux for 15 hours. After cooling the solid was filtered, and the filtrate was concentrated, washed with ethyl ether. The washing was concentrated further to a solid. Additional washing with cold ethyl ether (10 mL) afforded N-(4-chlorophenyl)-2-aminobenzamide as a tan solid; NMR (DMSO-d6) 10.1 (s, 1), 7.8 (d, 2), 7.6 (d, 1), 7.4 (d, 2), 7.2 (t, 1), 6.8 (d, 1), 6.6 (t, 1), 6.3 (s,2) ppm.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 15 hours
  3. temperatureAfter cooling the solid
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated
  6. washwashed with ethyl ether
  7. concentrationThe washing was concentrated further to a solid
  8. washAdditional washing with cold ethyl ether (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-8729302a4a2d440c832169802fb1e4fc
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498185B1

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