Tetrahydrofuran → 4-((2,6-Dinitrophenyl)amino)resorcinol

HRID 355683

Reaktionsgleichung

Reaktionsgleichung von HRID 355683
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl.[NH2:15][C:16]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][C:17]=1[OH:23].O1CCCC1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[N+:11]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[NH:15][C:16]1[CH:22]=[CH:21][C:19]([OH:20])=[CH:18][C:17]=1[OH:23])([O-:13])=[O:12]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 118141-Chloro-2,6-dinitrobenzeneHCID 81531DiisopropylethylamineHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Produkt 1

HCID 540632544-((2,6-Dinitrophenyl)amino)resorcinolAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6 g (30 mmol) of 1-chloro-2,6-dinitrobenzene and 4.8 g (30 mmol) of 4-aminoresorcinol hydrochloride were added to 300 ml of a mixture of tetrahydrofuran with dimethylformamide (1:1). After adding 7.8 g (60 mmol) of N,N-diisopropylethylamine thereto, the obtained mixture was stirred at room temperature for 24 hours. Then the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium chloride. Then it was dried over magnesium sulfate and concentrated and the residue was purified by silica gel column chromatography. Thus 6.95 g of 4-((2,6-dinitrophenyl)amino) resorcinol was obtained. This product was dissolved in 125 ml of dimethylformamide and 25 ml of N,N-diisopropylethyl-amine was added thereto. After heating at 100° C. for 2 hours, the reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and concentrated to dryness. Thus 5.4 g of the title compound was obtained.

Aufarbeitung

  1. distillationThen the solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialThen it was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-11d116a1b02e44bbad7779b9446031ff
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834462

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