2,4-Dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine → Methyl 4-((4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)-2-(3-chloropropoxy)benzoate

HRID 400361Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400361
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:3]=1.[NH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([O:26][CH2:27][CH2:28][CH2:29][Cl:30])[CH:17]=1>C1COCC1.C(Cl)Cl.O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[N:3]=[C:2]([NH:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([O:26][CH2:27][CH2:28][CH2:29][Cl:30])[CH:17]=2)[N:7]=1

Komponenten

6

Edukt 2

HCID 580396362,4-Dichloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazineHCID 67284899Methyl 4-amino-2-(3-chloropropoxy)benzoate

Produkt 1

HCID 86664102Methyl 4-((4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)-2-(3-chloropropoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe organic layer was collected
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by silica gel chromatography
  5. customThe product fractions were collected
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-58ee575fb1c44abf9b534308bd2b810c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741884B2

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