반응 #353192

ord-3df0456a7ca74d57b237eb52670e29ae

반응 조건

온도
0°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타To a 1 L three-necked round bottomed flask equipped with a magnetic stir bar
  2. 2
    온도reflux
  3. 3
    workup.ADDITIONcondenser and addition funnel
  4. 4
    workup.ADDITIONAfter the addition
  5. 5
    온도to warm to ambient temperature
  6. 6
    온도The flask was then cooled to 0° C.
  7. 7
    기타the layers were separated
  8. 8
    세척The organic layer was washed with H2O (50 mL), 0.05N NaOH (2×50 mL), H2O (50 mL), 1N HCl (3×50 mL) and H2O (2×50 mL)
  9. 9
    건조was dried over anhydrous Na2SO4
  10. 10
    여과The solution was filtered
  11. 11
    농축concentrated to a brown solid
  12. 12
    여과The solid was collected by filtration
  13. 13
    세척washed with 2-propanol (2×30 mL) and diethylether (2×40 mL)
  14. 14
    기타dried

실험 절차

To a 1 L three-necked round bottomed flask equipped with a magnetic stir bar, reflux condenser and addition funnel, was added chloroacetyl chloride (9.6 mL, 0.120 mol) and CHCl3 (100 mL). The addition funnel was charged with a solution of tetrahydroquinoxaline (8.0 g, 0.0596 mol) and triethylamine (20.8 mL) in CHCl3 (100 mL). The flask was chilled to 0° C., and the amine was slowly added to the acid chloride. After the addition was complete, the mixture was allowed to warm to ambient temperature and stir for 1 hour. The flask was then cooled to 0° C. and H2O (50 mL) was slowly added. The mixture was diluted with CHCl3 (250 mL) and the layers were separated. The organic layer was washed with H2O (50 mL), 0.05N NaOH (2×50 mL), H2O (50 mL), 1N HCl (3×50 mL) and H2O (2×50 mL), and was dried over anhydrous Na2SO4. The solution was filtered and concentrated to a brown solid. The solid was collected by filtration, washed with 2-propanol (2×30 mL) and diethylether (2×40 mL) and dried to yield the title product (4.41 g, 51.5%). 1H NMR (DMSO-d6): δ 3.89 (s, 4 H), 4.01 (s, 4 H), 7.25 (s, 2 H), 7.65 (br s, 2 H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05650133uspto-grants-1997_07