Water → HCID 178517481, Verbindung

HRID 2171543

Reaktionsgleichung

Reaktionsgleichung von HRID 2171543
[C:1]([CH:3]=[C:4]([NH:13][C:14](=O)[O:15]CC)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])#[N:2].[F:19][C:20]([F:26])([F:25])[C:21]([NH:23][NH2:24])=O.O.C(OCC)(=O)C>CN1C(=O)CCC1>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:4]1[N:13]=[C:14]([OH:15])[N:24]2[N:23]=[C:21]([C:20]([F:26])([F:25])[F:19])[N:2]=[C:1]2[CH:3]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 229753TrifluoroacetohydrazideHCID 76754608Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

Produkt 1

HCID 178517481HCID 178517481, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

2.10 g (7.4 mmol) of ethyl [2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate (Example 128A) and 0.95 g (7.4 mmol) of 2,2,2-trifluoroacetohydrazide are dissolved in NMP (10 ml) under argon and stirred in a flask with a calcium chloride drying tube at an oil-bath temperature of 160° C. for 4 h. The reaction mixture is cooled to RT, and water (20 ml) is added. Ethyl acetate (150 ml) and water (100 ml) are added, and the organic phase is separated off, dried with magnesium sulphate and concentrated. The residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 4:1 to 1:1). 0.97 g (38% of theory) of the product is obtained.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to RT
  2. customthe organic phase is separated off
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 4:1 to 1:1)
  6. custom0.97 g (38% of theory) of the product is obtained

Quellen und Nachweise

ORD-Eintrag
ord-6d26897bf9ba4dfca33cb1ca490449c7
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051323B2

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