Toluene → HCID 23134773, Verbindung

HRID 2220151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220151
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>O1CCOCC1>[CH2:8]([O:7][C:5]([C:4]1[CH:3]=[C:2]([NH:1][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])=[CH:19][CH:20]=2)[CH:12]=[CH:11][CH:10]=1)=[O:6])[CH3:9]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 11400Ethyl 3-aminobenzoateHCID 81531DiisopropylethylamineHCID 14916089Methyl 4-(bromomethyl)-α-oxobenzeneacetate

Produkt 1

HCID 23134773HCID 23134773, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of ethyl 3-aminobenzoate (7.3 ml) and methyl 2-[4-(bromomethyl)phenyl]-2-oxoacetate (6.4 g) in dioxane (40 ml) was added diisopropylethylamine (6.4 ml), and the mixture was stirred at 60° C. for 2 hrs. The mixture was allowed to return to room temperature and toluene (330 ml) was added. The mixture was left standing at 0° C. for 5 hrs and the precipitated diisopropylethylamine hydrobromide was filtered off. The filtrate was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate and water. The ethyl acetate layer was separated, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate:4-1 v/v) to give the object compound (7.61 g) as a syrup.

Aufarbeitung

  1. customto return to room temperature
  2. waitThe mixture was left
  3. waitstanding at 0° C. for 5 hrs
  4. filtrationthe precipitated diisopropylethylamine hydrobromide was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. customThe ethyl acetate layer was separated
  8. washwashed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c4107cb7271420eafae2ff9ee63e833
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417052B2

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