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N-bromobutanimide → Ethyl (4-methoxy-2-nitrobenzyl)aminoacetate

HRID 2417513
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2417513
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.C1C(C(OO)=O)=CC=CC=1.BrN1C(=O)CCC1=O.Cl.[CH2:32]([O:34][C:35](=[O:38])[CH2:36][NH2:37])[CH3:33].C(=O)([O-])O.[Na+]>C(O)C.C(OCC)(=O)C.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:37][CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:38])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 67184N-bromobutanimideHCID 871374-Methyl-3-nitroanisoleHCID 516892Sodium BicarbonateHCID 523077Perbenzoic acidHCID 2723640Glycine ethyl ester, hydrochloride

Produkt 1

HCID 86589883Ethyl (4-methoxy-2-nitrobenzyl)aminoacetate

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 241BenzeneLösungsmittelHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5.0 g (29 mmol) of 4-methoxy-1-methyl-2-nitrobenzene was added to a mixture of 50 ml of benzene, 50 ml of perbenzoic acid and 8 g (45 mmol) of N-bromosuccinimide, and they were stirred at 80° C. for one day. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 50 ml of ethanol. 8.4 g (60 mmol) of glycine ethyl ester hydrochloride and 5.0 g (60 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. overnight. The solvent was evaporated. After the extraction with ethyl acetate, the extract was washed with 1 N hydrochloric acid. The obtained aqueous layer was made basic with 1 N sodium hydroxide. After the extraction with ethyl acetate, the obtained organic layer was washed with saturated aqueous sodium chloride solution and then dried. The solvent was evaporated to obtain the title compound.

Aufarbeitung

  1. stirringwere stirred at 70° C. overnight
  2. customThe solvent was evaporated
  3. extractionAfter the extraction with ethyl acetate
  4. washthe extract was washed with 1 N hydrochloric acid
  5. extractionAfter the extraction with ethyl acetate
  6. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  7. customdried
  8. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7edad9d9174f4994a96f9e2e856f35ba
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06825191B2

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