Hippuric Acid → N-{2-Oxo-2-[(2-phenylpropan-2-yl)amino]ethyl}benzamide

HRID 1200147Notes

Reaction equation

HRID 1200147 reaction equation
[CH3:1][C:2]([NH2:10])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:30](O)(=[O:41])[CH2:31][NH:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34].C1C=C(SSC2N=CC=CC=2)N=CC=1>C(Cl)Cl>[CH3:1][C:2]([NH:10][C:30](=[O:41])[CH2:31][NH:32][C:33](=[O:34])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 464Hippuric AcidHCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 68509Cumylamine

Product 1

HCID 13649252N-{2-Oxo-2-[(2-phenylpropan-2-yl)amino]ethyl}benzamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 g of α,α-dimethylbenzylamine and 1.95 g of triphenylphosphine were dissolved in 100 ml of anhydrous methylene chloride. 1.33 g of hippuric acid and 1.63 g of 2,2'-dipyridyl disulfide were added in that order to the solution, and the mixture was heated under reflux for 2 hours. At the end of this time, the reaction solution was washed with a 10% w/v aqueous solution of sodium hydroxide and then with 1N aqueous hydrochloric acid, and dried over anhydrous sodium sulfate After concentration of the reaction solution by evaporation under reduced pressure, the resulting residue was subjected to silica gel column chromatography for separation and purification (using as eluent a 1:1 by volume mixture of hexane and ethyl acetate), to give 1.97 g (yield 90%) of the title product melting at 156°-157° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washAt the end of this time, the reaction solution was washed with a 10% w/v aqueous solution of sodium hydroxide
  4. dry with materialwith 1N aqueous hydrochloric acid, and dried over anhydrous sodium sulfate After concentration of the reaction solution
  5. customby evaporation under reduced pressure
  6. customthe resulting residue was subjected to silica gel column chromatography for separation and purification (
  7. additionby volume mixture of hexane and ethyl acetate),

Sources & evidence

ORD record
ord-40cb0684b9224d38923a3ed32dc8b173
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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