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Dimethylformamide → 3-(5-Methyl-2-phenyl-4-oxazolyl)propanamide

HRID 1294179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1294179
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([OH:17])=O.C[N:19](C)C=O.C(Cl)(=O)C(Cl)=O>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([NH2:19])=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 120932643-(5-Methyl-2-phenyl-4-oxazolyl)propionic acid

Produkt 1

HCID 178613843-(5-Methyl-2-phenyl-4-oxazolyl)propanamideAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 3-(5-methyl-2-phenyl-4-oxazolyl)propionic acid (20.0 g), N,N-dimethylformamide (0.5 mL) and tetrahydrofuran; (300 mL) was dropwise added oxalyl chloride (13.18 g) under ice-cooling, and the mixture was stirred at room temperature for 1.5 hrs. The reaction mixture was concentrated, and the obtained residue was dissolved in tetrahydrofuran (100 mL). This solution was dropwise added to a mixture of 25% aqueous ammonia (200 mL) and tetrahydrofuran (100 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 hrs and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give crystals (15.4 g, 77%) of 3-(5-methyl-2-phenyl-4-oxazolyl)propanamide. Recrystallization from chloroform-ethanol gave colorless prism crystals. melting point: 149-150° C.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe obtained residue was dissolved in tetrahydrofuran (100 mL)
  4. additionThis solution was dropwise added to a mixture of 25% aqueous ammonia (200 mL) and tetrahydrofuran (100 mL) at room temperature
  5. stirringThe reaction mixture was stirred at room temperature for 1.5 hrs
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a756a3d0eecf468d810e68257571c3f3
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07238716B2

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