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

HRID 844154Notes

Reaction equation

HRID 844154 reaction equation
[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

Participants

3

Reactant 2

HCID 78124-ChloroanilineHCID 312751,4-Dioxane

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7239689035fc4afeb8574d5c49e021ae
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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