2-Furancarboxylic acid → HCID 53466685, Verbindung

HRID 532501

Reaktionsgleichung

Reaktionsgleichung von HRID 532501
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.S(Cl)(Cl)=O.[N:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][N:14]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.ClCCl>[N:13]1[CH:18]=[CH:17][C:16]([NH:19][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:15][N:14]=1

Komponenten

8

Edukt 4

HCID 69192-Furancarboxylic acidHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 2984924-Aminopyridazine

Produkt 1

HCID 53466685HCID 53466685, VerbindungAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.00 g (17.8 mmol) of furan-2-carboxylic acid were suspended in 25 mL of toluene and one drop of dimethylformamide was added to the mixture. 1.95 ml of thionylchloride (26.8 mmol) were added at room temperature and the reaction mixture was stirred at 80° C. for two hours. After removal of the solvent, toluene was added and the evaporation was repeated. The obtained residue was then dissolved in 5 ml of dichloromethane and the solution was added dropwise to a solution containing 1.70 g of pyridazin-4-yl-amine (17.8 mmol) and 2.73 ml of triethyl amine (19.6 mmol) in 20 ml of dichloromethane. The mixture was stirred at room temperature for 2 days and washed twice with water. The organic layer was dried over Na2SO4, filtered and the solvent was removed under vacuum to give the title compound as a brown solid (1.9 g, 54%, 95% purity).

Aufarbeitung

  1. customAfter removal of the solvent, toluene
  2. additionwas added
  3. customthe evaporation
  4. dissolutionThe obtained residue was then dissolved in 5 ml of dichloromethane
  5. additionthe solution was added dropwise to a solution
  6. stirringThe mixture was stirred at room temperature for 2 days
  7. washwashed twice with water
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9e73f97379574813b8ff767d2c420869
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853214B2

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