Potassium Carbonate → 1-(2-Amino-3-nitrophenoxy)-2,3-epoxypropane

HRID 896007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896007
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12]([CH:14]1[O:16][CH2:15]1)Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:8]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:11][CH2:12][CH:14]2[CH2:15][O:16]2)[C:2]=1[NH2:1])([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 41154952-Amino-3-Nitrophenol

Produkt 1

HCID 113448381-(2-Amino-3-nitrophenoxy)-2,3-epoxypropaneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 2-amino-3-nitro-phenol (18.0 g, 0.117 mol) and epibromohydrin (21.0 g, 0.15 mol) in DMF (200 mL) containing potassium carbonate (20.7 g, 0.15 mol) was stirred at 70° C. overnight. The mixture was evaporated in vacuo, water was added to the residue and the mixture was then extracted with dichloromethane (2×300 mL), the combined organic layers were washed with saturated sodium chloride (300 mL), dried and concentrated. Purification by flash column chromatography (silica gel, methylene chloride) provided 15.0 g of the title compound as an orange solid. 1H NMR (DMSO-d6): δ 7.60 (dd, 1H); 7.11 (dd, 1H); 7.05 (s, 2H); 6.60 (dd, 1H); 4.40 (dd, 1H); 3.93 (dd, 1H); 3.42 (m, 1H); 2.87 (dd, 1H); 2.75 (dd, 1H).

Aufarbeitung

  1. customThe mixture was evaporated in vacuo, water
  2. additionwas added to the residue
  3. extractionthe mixture was then extracted with dichloromethane (2×300 mL)
  4. washthe combined organic layers were washed with saturated sodium chloride (300 mL)
  5. customdried
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-17a455429cd94a4aa2dc136f98415035
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919334B2

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