Methyl iodide → 3-Ethoxycarbonyl-2-methylthio-4-oxo-6,7,8-trifluoro-4H-1-benzothiopyran

HRID 5357

Reaktionsgleichung

Reaktionsgleichung von HRID 5357
F[C:2]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[CH:12][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[C:19](=[S:21])=[S:20].[CH2:22](N(CC)CC)C.CI>CS(C)=O>[CH2:10]([O:9][C:7]([C:6]1[C:4](=[O:5])[C:3]2[CH:12]=[C:13]([F:18])[C:14]([F:17])=[C:15]([F:16])[C:2]=2[S:20][C:19]=1[S:21][CH3:22])=[O:8])[CH3:11]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

Produkt 1

HCID 217702223-Ethoxycarbonyl-2-methylthio-4-oxo-6,7,8-trifluoro-4H-1-benzothiopyranAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 3.00 g (11.4 mmol) of ethyl 2,3,4,5-tetrafluorobenzoylacetate, 870 mg (11.4 mmol) of carbon disulfide and 9 ml of dried dimethyl sulfoxide were added 2.31 g (22.8 mmol) of triethylamine at room temperature, and the mixture was stirred for 1 hour at room temperature. Then, at room temperature, 3.24 g (22.8 mmol) of methyl iodide were added and the mixture was stirred for 2 hours, which was poured into ice-water. The crystals deposited were collected by filtration and dried to obtain 2.81 g (8.41 mmol) of title compound (yield 74%.

Aufarbeitung

  1. stirringthe mixture was stirred for 2 hours
  2. filtrationThe crystals deposited were collected by filtration
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-93c2e2181a674049914d3893aea5bed6
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244892

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