Bromoacetyl bromide → {2-[(2-Bromoacetyl)-(2-chlorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

HRID 1694890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1694890
[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]([O:10][C:11](=[O:25])[NH:12][C:13]([CH3:24])([CH3:23])[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])([CH3:9])([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+]>CN(C)C(=O)C>[C:6]([O:10][C:11](=[O:25])[NH:12][C:13]([CH3:24])([CH3:23])[CH2:14][N:15]([C:3](=[O:4])[CH2:2][Br:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])([CH3:9])([CH3:7])[CH3:8]

Komponenten

5

Edukt 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 66645795[2-(2-Chlorophenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester

Produkt 1

HCID 66645498{2-[(2-Bromoacetyl)-(2-chlorophenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl esterAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

1.52 ml of bromoacetyl bromide (17.5 mmol) was added to a solution of 3.49 g of [2-(2-chlorophenylamino)-1,1-dimethylethyl]carbamic acid t-butyl ester obtained in Example (1h) (11.7 mmol) in N,N-dimethylacetamide (58 ml) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hexane was added to the residue, and the solid was collected by filtration to obtain 4.68 g of the title compound (yield: 95%).

Aufarbeitung

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThen, the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. additionHexane was added to the residue
  8. filtrationthe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-715ae6a2630a45898b945ea0f2aed6cb
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158790B2

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