Diisopropylethylamine → 1-(2-(3,5-Dichlorobenzylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

HRID 1910566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910566
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1F)=[O:4].[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:19][NH2:20].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:19][NH:20][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[C:2]([F:14])([F:13])[F:1]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 457602Benzenemethanamine, 3,5-dichloro-HCID 247268371-(2,4-Difluorophenyl)-2,2,2-trifluoroethanone

Produkt 1

HCID 587073441-(2-(3,5-Dichlorobenzylamino)-4-fluorophenyl)-2,2,2-trifluoroethanoneAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2,2,2,2′,4′-pentafluoroacetophenone (1.05 g, 5.0 mmol), 3,5-dichlorobenzylamine (0.88 g, 5.0 mmol), N,N-diisopropylethylamine (1.7 mL, 10.0 mmol) and acetonitrile (25 mL) was heated at reflux for 18 h, cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate; this solution was washed with water, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using 5% ethyl acetate in hexanes as eluent to yield the title compounds as a yellowish solid (0.78 g, 43%). 1H NMR (400 MHz, CDCl3): δ 9.28 (br s, 1 H), 7.88 (m, 1 H), 7.34 (s, 1 H), 7.22 (s, 2 H), 6.44 (m, 1 H), 6.30 (dd, 1 H), 4.43 (d, 2 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washthis solution was washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography on silica gel using 5% ethyl acetate in hexanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ae99f53e3cea4b3fa834e27091d749a7
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604021B2

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