Sodium Chloride → HCID 19082296, Verbindung

HRID 1580856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1580856
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][CH2:15][NH2:16])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20].[OH-].[Na+].[Cl-].[Na+]>CS(C)=O>[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][CH2:15][NH2:16])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 189583303-Nitrotyramine

Produkt 1

HCID 19082296HCID 19082296, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of 17.1 g. (0.1 m.) of benzyl bromide in 100 ml. of dimethylsulfoxide is added slowly to a stirred mixture of 18.2 g. (0.1 m.) of 4-hydroxy-3-nitrophenethylamine in 1 l. of dimethylsulfoxide and 60 ml. of 2N sodium hydroxide at 85°C. After addition is complete the reaction mixture is stirred at 85°C. for an additional two hours, poured into ice-water, saturated with sodium chloride and extracted with ethyl acetate. The organic extract is dried and concentrated to give 4-benzyloxy-3-nitrophenethylamine. The latter (2.72 g., 0.01 m.) in 50 ml. of toluene is rfluxed azeotropically with 1.27 g. (0.012 m.) of benzaldehyde until water formation is completed (about one hour). Solvent is removed by distillation to leave the crude imine. Sodium borohydride (0.38 g., 0.01 m.) is then added to a solution of the above imine in 30 ml. of methanol over a period of 30 minutes and after stirring for an additional hour the reaction mixture is evaporated. The residue is treated with 2N hydrochloric acid and ether. The solid obtained is filtered and washed to give N-benzyl-4-benzyloxy-3-nitrophenethylamine hydrochloride.

Aufarbeitung

  1. customat 85°C
  2. additionAfter addition
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. customis dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-56efa7960c694845a06911942b8aea89
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03933913

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