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Ammonia → HCID 19348480, Verbindung

HRID 1418194
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1418194
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2].[NH3:17].C(OCC)(=O)C.CCCCCC>C(#N)C.C(OCC)(=O)C.CCCCCC>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](=[O:10])[NH2:17])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 8058HexaneHCID 8857Ethyl AcetateHCID 7388134-Tert-butyl-3-nitrobenzoic acid

Produkt 1

HCID 19348480HCID 19348480, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342Acetonitrile
Lösungsmittel
HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

12.0 g (74.0 mmol) of N,N'-carbonyldiimidazole were added to a suspension of 15.03 g (67.3 mmol) of 4-t-butyl-3-nitrobenzoic acid in 150 ml of acetonitrile, and the resulting mixture was stirred for 1 hour, after which 20 ml (0.31 mol) of aqueous ammonia were added. The reaction mixture was stirred for 30 minutes, after which it was concentrated by evaporation under reduced pressure, and the concentrate was dissolved in ethyl acetate. The organic phase was washed with water, with 2N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 150 g of silica gel, using a gradient elution method, with mixtures of ethyl acetate and hexane ranging from 1:1 to 2:1 by volume as the eluent, to give 12.68 g (yield 85%) of the title compound as crystals, melting at 114°-115° C. (from ethyl acetate-hexane).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. concentrationafter which it was concentrated by evaporation under reduced pressure
  3. dissolutionthe concentrate was dissolved in ethyl acetate
  4. washThe organic phase was washed with water, with 2N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through 150 g of silica gel
  8. washa gradient elution method

Quellen und Nachweise

ORD-Eintrag
ord-ea541de061ea4c2781ff3dee86bdf6c1
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05880147

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