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

HRID 610080

Reaction equation

HRID 610080 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 196009793-(3,3-Diphenyl-ureido)-N-phenylbenzamideYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b4ea39b9f4e54985812f70768033485a
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Linked notes

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