Triethylamine → 3-(Chloromethyl)-5-[2-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazole

HRID 1188690

Reaktionsgleichung

Reaktionsgleichung von HRID 1188690
[Cl:1][CH2:2][C:3](=[NH:6])[NH:4][OH:5].C(N(CC)CC)C.[F:14][C:15]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:16]=1[C:17](Cl)=O>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]1[N:6]=[C:17]([C:16]2[CH:20]=[C:21]([C:24]([F:25])([F:27])[F:26])[CH:22]=[CH:23][C:15]=2[F:14])[O:5][N:4]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27348802-Fluoro-5-(trifluoromethyl)benzoyl ChlorideHCID 178511097HCID 178511097, Verbindung

Produkt 1

HCID 53117343-(Chloromethyl)-5-[2-fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleAusbeute 19,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-N-hydroxyethanimidamide (2.4 g, 22.1 mmol) and triethylamine (3.7 ml, 26.5 mmol) in dry toluene (35 mL) was added 2-fluoro-5-(trifluoromethyl)benzoyl chloride (5 g, 22.1 mmol) at 0° C. The mixture was stirred at room temperature for 1 h and then at 100° C. overnight. The resulting solid was filtered and the filtrate was then concentrated in vacuo. The residue was purified by radial chromatography (0-30% EtOAc-hexanes gradient) to afford the title compound (1.2 g, 19% yield): MS (ES) m/z 281 (M+1) and 283 (M+1, isotope).

Aufarbeitung

  1. customat 100° C.
  2. customovernight
  3. filtrationThe resulting solid was filtered
  4. concentrationthe filtrate was then concentrated in vacuo
  5. customThe residue was purified by radial chromatography (0-30% EtOAc-hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-ccf2428e311e4d4fa2b54d740fba0ef4
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673948B2

Verknüpfte Notizen

Wird geladen…