Triethylamine → 3-(3,3-Diphenyl-ureido)-N-phenylbenzamide

HRID 610080

Reaktionsgleichung

Reaktionsgleichung von HRID 610080
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].[C:17]1([N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C(O)C>[C:17]1([N:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24](=[O:25])[NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=2)[C:5]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:6])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chlorideHCID 843473-Aminobenzanilide

Produkt 1

HCID 196009793-(3,3-Diphenyl-ureido)-N-phenylbenzamideAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-N-phenylbenzamide (2.0 g, 9.4 mmol), diphenylcarbamoyl chloride (2.2 g, 9.4 mmol) and triethylamine (2.6 mL, 19 mmol) in ethanol (10 mL) was heated to reflux for 4.5 hours. The mixture was cooled and concentrated, water was added, the slurry was acidified with 1 N HCl and the solid was collected, washed with water, dried and recrystallized from acetone/hexanes, to give a colorless solid (1.63 g, 42%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. additionwater was added
  6. customthe solid was collected
  7. washwashed with water
  8. customdried
  9. customrecrystallized from acetone/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b4ea39b9f4e54985812f70768033485a
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998463

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