Acrylonitrile → Tralopyril

HRID 1358787

Reaktionsgleichung

Reaktionsgleichung von HRID 1358787
Cl[CH:2]([N:7]=[C:8](Cl)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3]([F:6])([F:5])[F:4].[C:17](#[N:20])[CH:18]=[CH2:19].C(N(CC)C(C)C)(C)C.[Br:30]Br>CN(C)C=O.CCCCCCC.C(OCC)(=O)C>[Br:30][C:19]1[C:18]([C:17]#[N:20])=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[NH:7][C:2]=1[C:3]([F:6])([F:5])[F:4]

Komponenten

8

Edukt 4

HCID 7855AcrylonitrileHCID 24408BromineHCID 81531DiisopropylethylamineHCID 72751476N-[1-chloro-(2,2,2-trifluoroethyl)]-4-chlorobenzimidoyl chloride

Produkt 1

HCID 183559TralopyrilAusbeute 22,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

A solution of N-[1-chloro-(2,2,2-trifluoroethyl)]-4-chlorobenzimidoyl chloride (5.80 g, 0.02 mol) and acrylonitrile (1.33 g, 0.025 mol) in N,N-dimethylformamide (15 mL) under a nitrogen atmosphere is treated with N,N-diisopropylethylamine (DIPEA, 7.8 g, 0.06 mol) over 30 minutes, heated to and held at 45-47° C. for 18 hours, cooled to room temperature, treated with bromine (3.2 g, 0.02 mol), stirred at room temperature for 1 hour, quenched with water, and extracted with ethyl acetate. The organic extract is concentrated in vacuo to obtain a residue. Flash column chromatography of the residue on silica gel, packed with 15% ethyl acetate in heptane and eluted with 20% ethyl acetate in heptane, gives the title product as white solid (1.6 g, 22.9% yield) which is identified by 1H and 19F NMR spectral analyses.

Aufarbeitung

  1. temperatureheated to and
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. concentrationis concentrated in vacuo
  6. customto obtain a residue
  7. washeluted with 20% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-cd3be75980be4c36b45f7bc664701e92
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596902B2

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