Hydrochloric Acid → HCID 15952779, Verbindung

HRID 1927323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927323
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:15])([F:14])[F:13])[CH:5]=1)=[C:2]=[S:3].[CH3:16][C:17]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])[C:18]#N.C[OH:29].Cl>CN(C=O)C.O>[C:22]1([N:21]2[C:17]([CH3:16])([CH3:20])[C:18](=[O:29])[N:1]([C:4]3[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([C:12]([F:13])([F:15])[F:14])[CH:5]=3)[C:2]2=[S:3])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 751282-Anilino-2-methylpropiononitrileHCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 15952779HCID 15952779, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1a (0.274 g, 1.2 mmol) and 6a (0.160 g, 1 mmol) in dry DMF (0.2 ml) was stirred for 48 h. To this mixture were added methanol (10 ml) and 2N HCl (3 ml). The second mixture was refluxed for 6 h. After being cooled to room temperature, the reaction mixture was poured into cold water (20 ml) and extracted with ethyl acetate (20 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane) to yield 4-[3-phenyl-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile, 6b, [RD10] (0.276 g, 0.71 mmol, 71%) as a white powder.

Aufarbeitung

  1. temperatureThe second mixture was refluxed for 6 h
  2. extractionextracted with ethyl acetate (20 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed (dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-16f5838901704cec9960ba67f8e0aa68
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183274B2

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