Ammonium Hydroxide → 4-Phenylbenzamide

HRID 497146Notes

Reaction equation

HRID 497146 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[OH-].[NH4+:23]>C(Cl)Cl.CN(C=O)C>[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH2:23])=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 66724(1,1'-Biphenyl)-4-carboxylic acid

Product 1

HCID 6025064-PhenylbenzamideYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-phenylbenzoic acid (5.46 g, 27.6 mmol) in methylene chloride (66 mL) was added 2 drops of DMF and oxalyl chloride (2.80 mL, 30.3 mmol). The reaction mixture was stirred overnight and added to a stirred solution of ice and ammonium hydroxide. The resulting precipitate was filtered, washed with methylene chloride, and triturated with water. The product was collected by filtration and dried in vacuo to yield 4-phenylbenzamide (3.88 g, 71%).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with methylene chloride
  3. customtriturated with water
  4. filtrationThe product was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-edb78f076c0240c1a2c2eb75f64ff353
Source dataset
uspto-grants-2005_09
Patent number
US06949559B2

Reaction notes

Loading…