Water → t-Butyl N-(2-benzoylphenyl)-N-(p-toluenesulfonyl)aminoacetate

HRID 1871817

Reaktionsgleichung

Reaktionsgleichung von HRID 1871817
[C:1]1([CH3:25])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11]2[CH:24]=[CH:23][CH:22]=[CH:21][C:12]=2[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].O>CN(C)C=O>[C:13]([C:12]1[CH:21]=[CH:22][CH:23]=[CH:24][C:11]=1[N:10]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:25])=[CH:6][CH:5]=1)(=[O:9])=[O:8])(=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 233206N-(2-Benzoylphenyl)-4-methylbenzenesulfonamide

Produkt 1

HCID 18688807t-Butyl N-(2-benzoylphenyl)-N-(p-toluenesulfonyl)aminoacetateAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 5.0 g of compound H in 10 cc of dimethylformamide was added 0.56 g of 63% sodium hydride in 5 cc of dimethylformamide under ice-cooling and the mixture was stirred for 30 minutes. Then, 2.3 cc of t-butyl bromoacetate was added dropwise at the same temperature and stirring was continued for 16 hours. Water was added to the reaction mixture and the desired compound was extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was distilled off and the crude product thus obtained was washed with hexane to obtain 6.31 g of compound I. Yield: 95.4%.

Aufarbeitung

  1. temperaturecooling
  2. stirringstirring
  3. waitwas continued for 16 hours
  4. extractionthe desired compound was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe crude product thus obtained
  9. washwas washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-aa24dcc414ce4a0db5e75eb596a02395
Quelldatensatz
uspto-grants-2000_08
Patentnummer
USRE036832

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