Ammonium Hydroxide → 3-(Benzyl)benzamide

HRID 411323Notes

Reaction equation

HRID 411323 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH4+:23].[OH-]>CN(C=O)C.C(Cl)Cl>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:23])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 41245533-Benzylbenzoic acid

Product 1

HCID 222388273-(Benzyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To the product from Step A (0.0119 moles) was added 150 mL of CH2Cl2, one drop of DMF, 10 mL of oxalyl chloride, and the mixture was stirred at room temperature for 3 hours. After cooling to 10° C., 30 mL of NH4OH (exothermic) was added and the mixture was stirred for 30 min. The reaction mixture was then concentrated and the resulting residue diluted with ethyl acetate. The organic layer was washed with 1N NaOH, brine, dried over Na2SO4, and concentrated to give the 3-(benzyl)benzamide as a white solid, which was used without further purification.

Workup

  1. temperatureAfter cooling to 10° C.
  2. stirringthe mixture was stirred for 30 min
  3. concentrationThe reaction mixture was then concentrated
  4. additionthe resulting residue diluted with ethyl acetate
  5. washThe organic layer was washed with 1N NaOH, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-53b7e3770932483fbc4f743a34f307ba
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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