Sodium Hydroxide → N-(2-Bromobenzyl)-2,2-diethoxyacetamide

HRID 1181410

Reaktionsgleichung

Reaktionsgleichung von HRID 1181410
[CH2:1]([O:3][CH:4]([O:10][CH2:11][CH3:12])[C:5]([O:7]CC)=O)[CH3:2].[OH-].[Na+].S(Cl)(Cl)=O.[Br:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23]>C(O)C.O.CCOCC.C1(C)C=CC=CC=1.N1C=CC=CC=1>[Br:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH:23][C:5](=[O:7])[CH:4]([O:3][CH2:1][CH3:2])[O:10][CH2:11][CH3:12]

Komponenten

10

Edukt 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 80169Ethyl diethoxyacetateHCID 3340722-Bromobenzylamine

Produkt 1

HCID 59636401N-(2-Bromobenzyl)-2,2-diethoxyacetamideAusbeute 44,9 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a solution of ethyl diethoxyacetate (20.0 g, 114 mmol) in ethanol (50 ml) was added a solution of sodium hydroxide (4.56 g, 114 mmol) in water (25 ml), and the resulting mixture heated at reflux for 5 hours. The mixture was evaporated to dryness, and the residue dried in vacuo. The resulting solid (22.75 g, 0.13 mol) was dissolved in dry ether (88 ml) and to this mixture was added thionyl chloride (13.3 g, 0.11 mol) with stirring for 10 minutes at 10° C. The reaction mixture was heated at reflux for 30 minutes and then allowed to cool. A solution of 2-bromobenzylamine (20.73 g, 0.11 mol) in toluene (57 ml) and pyridine (34 ml) was poured into this reaction mixture with vigorous stirring. This was heated at reflux for 30 minutes and then allowed to cool. The mixture was poured into ice water and extracted with toluene (×3). The organic extracts were combined and washed firstly with 2% HCl and then water. The solvent was evaporated and the residue purified by flash chromatography on silica gel (9:1 hexane:ethyl acetate) to give the title compound (15.6 g, 44%).

Aufarbeitung

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 5 hours
  3. customThe mixture was evaporated to dryness
  4. customthe residue dried in vacuo
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for 30 minutes
  7. temperatureto cool
  8. temperatureThis was heated
  9. temperatureat reflux for 30 minutes
  10. temperatureto cool
  11. extractionextracted with toluene (×3)
  12. washwashed firstly with 2% HCl
  13. customThe solvent was evaporated
  14. customthe residue purified by flash chromatography on silica gel (9:1 hexane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-685d4b4cd58444d6b866a2ba55de0109
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285563B2

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