Methyl Thioglycolate → Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

HRID 335565

Reaktionsgleichung

Cl[C:2]1[C:9]([C:10]#[N:11])=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[H-].[Na+].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[CH3:20]S(Cl)(=O)=O>C(OCC)(=O)C>[C:10]([C:9]1[CH:8]=[CH:7][C:6]2[CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[S:14][C:3]=2[CH:2]=1)#[N:11]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

2.5 g (15.1 mmol) of 2-chloro-3-cyanobenzaldehyde are reacted according to the general procedure with 0.90 g (22.7 mmol) of sodium hydride (60% pure) and 1.76 g (16.6 mmol) of methyl mercaptoacetate. The resulting reaction product is initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1) and then dissolved in 30 ml of pyridine, and 650 μl (8.4 mmol) of methanesulfonyl chloride are added. The mixture is stirred at 80° C. for 2 h. After cooling, ethyl acetate is added and the mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate, concentrated and dried under high vacuum. This gives 1.63 g (49.9% of theory) of the title compound.

Aufarbeitung

customThe resulting reaction product
customis initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1)
dissolutiondissolved in 30 ml of pyridine
temperatureAfter cooling
washthe mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated
customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag: ord-cadb99b348c0446fad0682c7241d51cb
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08884017B2

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