Reaktion #487543

ord-58ee575fb1c44abf9b534308bd2b810c

Reaktionsgleichung

FC(F)(F)COc1nc(Cl)nc(Cl)n1
2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine
COC(=O)c1ccc(N)cc1OCCCCl
methyl 4-amino-2-(3-chloropropoxy)benzoate
COC(=O)c1ccc(Nc2nc(Cl)nc(OCC(F)(F)F)n2)cc1OCCCCl
methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe organic layer was collected
  2. 2
    Trocknendried over sodium sulfate
  3. 3
    Einengenconcentrated under vacuum
  4. 4
    SonstigeThe crude product was purified by silica gel chromatography
  5. 5
    SonstigeThe product fractions were collected
  6. 6
    Einengenconcentrated under vacuum

Vorschrift

To a solution of 2,4-dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine (770 mg, 2.79 mmol) in THF (10 mL) was added methyl 4-amino-2-(3-chloropropoxy)benzoate (681 mg, 2.79 mmol) and Hunig'sBase (1.464 mL, 8.38 mmol). The resulting mixture was stirred for 16 h. The reaction was diluted with DCM and water. The organic layer was collected and dried over sodium sulfate, and concentrated under vacuum. The crude product was purified by silica gel chromatography using 20-40% EtOAc/Hexanes. The product fractions were collected and concentrated under vacuum to give methyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)-2-(3-chloropropoxy)benzoate as a solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08741884B2uspto-grants-2014_06