Methyl 2-chloroacrylate → HCID 11034029, Verbindung

HRID 849275

Reaktionsgleichung

Reaktionsgleichung von HRID 849275
[F:1][C:2]([F:15])([F:14])[CH2:3][N:4]=[C:5](Cl)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.Cl[C:17](=[CH2:22])[C:18]([O:20][CH3:21])=[O:19].N12CCCN=C1CCCCC2>CN(C)C=O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]2[NH:4][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 6659Methyl 2-chloroacrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11807271Benzenecarboximidoyl chloride, 4-chloro-N-(2,2,2-trifluoroethyl)-

Produkt 1

HCID 11034029HCID 11034029, VerbindungAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(2,2,2-trifluoroethyl)-4-chlorobenzimidoyl chloride (10.2 g, 0.04 mol) and methyl 2-chloroacrylate (5.8 g, 0.048 mol) in N,N-dimethylformamide is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 19.5 g, 0.128 mol) over 30 minutes at such a rate that the temperature is kept at 40° C., stirred for two hours, and quenched with water and ethyl acetate. The organic layer is separated, washed sequentially with aqueous HCl and water, and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and a 20% ethyl acetate in heptane solution and crystallization from heptane gives the title product as white crystals (4.2 g, 34.6% yield, mp 120.0-122.5° C.)

Aufarbeitung

  1. customis kept at 40° C.
  2. customquenched with water and ethyl acetate
  3. customThe organic layer is separated
  4. washwashed sequentially with aqueous HCl and water
  5. concentrationconcentrated in vacuo
  6. customto obtain an oil
  7. customa 20% ethyl acetate in heptane solution and crystallization from heptane

Quellen und Nachweise

ORD-Eintrag
ord-1b29870133c948a0bbe0386f4ccf5867
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06011161

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