1,1'-Carbonyldiimidazole → HCID 178505356, Verbindung

HRID 898816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898816
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].FC1C=CC=CC=1C1OC(C([NH:47][C:48]([NH2:50])=[NH:49])=O)=CC=1>C1COCC1.[Cl-].[Na+].O>[CH3:28][S:29]([OH:32])(=[O:31])=[O:30].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([NH:49][C:48]([NH2:50])=[NH:47])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 7266935-(4-Chlorophenyl)-2-furoic acidHCID 178505355HCID 178505355, Verbindung

Produkt 1

HCID 178505356HCID 178505356, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

5-(4-chlorophenyl)furan-2-carboxylic acid (208 mg, 0.93 mmol) was dissolved in THF (5 ml), to which 1,1′-carbonyldiimidazole (CDI) (182 mg, 1.12 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. 2 M guanidine solution (2.73 ml, 5.45 mmol) prepared in Example 1 was added thereto, and the mixture was reacted at room temperature for 12 hours. After completion of the reaction, the solution was added with saturated brine (20 ml) and extracted with ethyl acetate (30 ml×3). The organic layer was washed with 10% brine, dried over anhydrous magnesium sulfate (MgSO4), and concentrated in vacuo. The residue was dissolved in acetone (4 ml), to which methanesulfonic acid (0.2 ml) was added and then cooled down to 0° C. to precipitate solid. The precipitated solid was collected by filtration to give 234 mg of a title compound (yield: 70%).

Aufarbeitung

  1. additionwas added
  2. customthe mixture was reacted at room temperature for 12 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (30 ml×3)
  5. washThe organic layer was washed with 10% brine
  6. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in acetone (4 ml), to which methanesulfonic acid (0.2 ml)
  9. additionwas added
  10. temperaturecooled down to 0° C.
  11. customto precipitate solid
  12. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-042427d2f23f4da49b04cd65e9a4fecb
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351843B2

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