Reaktion #531866

Reaktionsgleichung

Compound 978

1-(3-Chloro-phenyl)-3-(1-hydroxymethyl-pentyl)-urea

POCl3

→

(4-Butyl-4,5-dihydro-oxazol-2-yl)-(3-chloro-phenyl)-amine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed via reduced pressure distillation
2. 2
   WaschenThe residue was washed with aqueous sodium bicarbonate
3. 3
   workup.DISSOLUTIONdissolved in EtOAc
4. 4
   SonstigeThe solvent was dried
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in acetone (1 mL)
8. 8
   Temperaturrefluxed with water (2 mL) for 1.5 hrs
9. 9
   ExtraktionThe solution was extracted with EtOAc
10. 10
    Sonstigethe organic layer evaporated
11. 11
    Sonstigethe residue chromatographed on silica
12. 12
    Sonstigeto give the target compound

Vorschrift

Compound 978 (50 mg) was treated with POCl3 (1.0 mL). This was stirred overnight. The solvent was removed via reduced pressure distillation. The residue was washed with aqueous sodium bicarbonate and then dissolved in EtOAc. The solvent was dried, filtered and evaporated. The residue was dissolved in acetone (1 mL) and refluxed with water (2 mL) for 1.5 hrs. The solution was extracted with EtOAc, the organic layer evaporated and the residue chromatographed on silica to give the target compound. 1H NMR (300 MHz, CDCl3) δ=7.38 (s, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.05 (br, 1H), 7.00 (d, 7.5 Hz, 1H), 4.47 (m, 1H), 3.95 (m, 2H), 1.8-1.2 (m, 6H), 0.95 (m, 3H). ESIMS=224.9 m/z (M+H)

Quelle