Water → Diethyl[2-(4-nitrophenoxy)ethyl]amine

HRID 639374

Reaktionsgleichung

Reaktionsgleichung von HRID 639374
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][OH:16])[CH3:12].[H-].[Na+].O>CN(C=O)C>[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][O:16][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[CH3:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 7497DiethylethanolamineHCID 24758Sodium hydride

Produkt 1

HCID 88294Diethyl[2-(4-nitrophenoxy)ethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the solution of 8.0 g (51 mMol) of 1-chloro-4-nitrobenzene and 6.0 g (6.8 mL; 51 mMol) of 2-diethylamino-ethanol in 50 mL of DMF at 0° C. is added 2.7 g of NaH portionwise over 2 h. After stirring another hour at rt, the reaction mixture is poured onto 300 mL of water and stirred. After filtering off some crystalline product, the aqeous layers are extracted with ethyl acetate. The combined organic layers are dried and evaporated to obtain diethyl-[2-(4-nitro-phenoxy)-ethyl]-amine. Title compound: ES-MS: 239 [M+H]+; single peak at tR=5.1 min (System 2).

Aufarbeitung

  1. stirringstirred
  2. filtrationAfter filtering off some crystalline product
  3. extractionthe aqeous layers are extracted with ethyl acetate
  4. customThe combined organic layers are dried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-aaa24246a16946cd9d2ca032d71d0226
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691855B2

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