Tetrahydrofuran → N-[4-cyano-3-(trifluoromethyl)phenyl]-2,2,4-trimethyl-1,3-dioxolane-4-carboxamide

HRID 457262

Reaktionsgleichung

Reaktionsgleichung von HRID 457262
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[Na].[CH2-:8][C:9]([CH3:11])=O.[C:12]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][C:15]=1[C:21]([F:24])([F:23])[F:22])#[N:13].[C:25]([O-:28])(O)=O.[Na+].O1CCC[CH2:31]1>C(N(CC)CC)C.CC(N(C)C)=O.C(OCC)(=O)C.CCCCCCC>[C:12]([C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]([C:1]2([CH3:31])[CH2:25][O:28][C:9]([CH3:11])([CH3:8])[O:5]2)=[O:3])=[CH:16][C:15]=1[C:21]([F:22])([F:23])[F:24])#[N:13]

Komponenten

10

Edukt 6

HCID 8028TetrahydrofuranHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 5360545SodiumHCID 178477758HCID 178477758, Verbindung

Produkt 1

HCID 22641284N-[4-cyano-3-(trifluoromethyl)phenyl]-2,2,4-trimethyl-1,3-dioxolane-4-carboxamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineLösungsmittelHCID 31374DimethylacetamideLösungsmittel2×HCID 21899848Ethylacetate heptaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

In a 50 ml 3-necked flask, equipped with a magnetic stirrer, under nitrogen at −20° C., 0.3 ml of oxalyl chloride in 1 ml of tetrahydrofuran was added slowly to 0.364 g of the sodium salt of the Example 5 (compound (8), R=Na) in a mixture of 0.5 ml of triethyl amine in 5 ml of dimethylacetamide. The resulting mixture was stirred for 30 minutes at −10° C. Then, a solution of 0.372 g of 4-cyano-3-trifluoromethylaniline in 2 ml of dimethylacetamide was added dropwise and slowly. The conversion was followed by TLC analysis (eluens:ethyl acetate/heptane=2/3). After ˜1 hour at room temperature, the reaction mixture was poured into 200 ml of saturated aqueous NaHCO3 solution, and was subsequently extracted with 2×30 ml of ethyl acetate. The combined organic layers were washed with 50 ml of brine, dried (Na2SO4) and concentrated at reduced pressure to give a dark-brown oil, which was purified by column chromatography (Merck 60 SiO2, eluens ethyl acetate/heptane=2/3). Isolated yield: 0.336 g light brown clear oil (51%). 1H-NMR confirmed the structure.

Aufarbeitung

  1. customIn a 50 ml 3-necked flask, equipped with a magnetic stirrer, under nitrogen at −20° C.
  2. waitAfter ˜1 hour at room temperature
  3. extractionwas subsequently extracted with 2×30 ml of ethyl acetate
  4. washThe combined organic layers were washed with 50 ml of brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated at reduced pressure
  7. customto give a dark-brown oil, which
  8. customwas purified by column chromatography (Merck 60 SiO2, eluens ethyl acetate/heptane=2/3)

Quellen und Nachweise

ORD-Eintrag
ord-e1d739268dd64645b0623e8dbdcca46f
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186854B2

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