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

HRID 1200147노트

반응식

HRID 1200147 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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),

출처 및 근거

ORD 기록
ord-40cb0684b9224d38923a3ed32dc8b173
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904680

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