Reaction #531866

Reaction equation

Compound 978

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

POCl3

→

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

Conditions

Workup

1. 1
   OtherThe solvent was removed via reduced pressure distillation
2. 2
   WashThe residue was washed with aqueous sodium bicarbonate
3. 3
   workup.DISSOLUTIONdissolved in EtOAc
4. 4
   OtherThe solvent was dried
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in acetone (1 mL)
8. 8
   Temperaturerefluxed with water (2 mL) for 1.5 hrs
9. 9
   ExtractionThe solution was extracted with EtOAc
10. 10
    Otherthe organic layer evaporated
11. 11
    Otherthe residue chromatographed on silica
12. 12
    Otherto give the target compound

Procedure

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)

Source