3-Chlorobenzoic Acid → HCID 58019514, Verbindung

HRID 330718

Reaktionsgleichung

Reaktionsgleichung von HRID 330718
ClC1C=C(C=CC=1)C(O)=[O:6].O.[N:12]1[C:21]2[C:16](=[C:17]3[CH:29]=[CH:28][CH:27]=[CH:26][C:18]3=[C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]3=2)[N:15]=[CH:14][CH:13]=1>ClCCl>[N+:12]1([O-:6])[C:21]2[C:16](=[C:17]3[CH:29]=[CH:28][CH:27]=[CH:26][C:18]3=[C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]3=2)[N:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 4473-Chlorobenzoic AcidHCID 962WaterHCID 252644Dibenzo(f,h)quinoxaline

Produkt 1

HCID 58019514HCID 58019514, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

First, to a solution in which 1.36 g of dibenzo[f,h]quinoxaline was dissolved in 20 mL of dichloromethane was added 2.04 g of 3-chlorobenzoic acid (abbreviation: MCPBA) in a nitrogen atmosphere, followed by stirring at room temperature for 1 week. Water was added to this mixture, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. Then, the resulting solution was filtered. The solvent of this solution was distilled off. The resulting residue was purified by silica gel column chromatography which uses a mixed solvent of dichloromethane and ethyl acetate as a developing layer. By recrystallization from dichloromethane, the object of the synthesis was obtained (as a white powder in a yield of 51%). The synthesis scheme of Step 1 is illustrated in the following (a″′-2-1).

Aufarbeitung

  1. extractionthe organic layer was extracted with dichloromethane
  2. washThe obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThen, the resulting solution was filtered
  5. distillationThe solvent of this solution was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography which
  7. customBy recrystallization from dichloromethane
  8. customthe object of the synthesis was obtained (as a white powder in a yield of 51%)
  9. customThe synthesis scheme of Step 1

Quellen und Nachweise

ORD-Eintrag
ord-c39679544a5f462f8753084078463a6e
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877351B2

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