Dimethylformamide → 4,4-Difluoro-3-methyl-3-butenyl 4-methyl-2-phenylthiazole-5-carboxylate

HRID 917381

Reaktionsgleichung

CN(C)C=O.CS([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])(=O)=O.[CH3:18][C:19]1[N:20]=[C:21]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:22][C:23]=1[C:24](O)=[O:25].C(=O)([O-])O.[Na+]>O>[CH3:18][C:19]1[N:20]=[C:21]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:22][C:23]=1[C:24]([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:15])[F:16])=[O:25]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To 25 ml of N,N-dimethylformamide were dissolved 2.60 g (13 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate and 2.19 g (10 mmol) of 4-methyl-2-phenylthiazole-5-carboxylic acid, followed by the addition of 1.68 g (20 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate ether: hexane=1:9) to obtain 3.03 g (yield: 94%) of 4,4-difluoro-3-methyl-3-butenyl 4-methyl-2-phenylthiazole-5-carboxylate.

Aufarbeitung

customThe reaction liquid
extractionextracted with diethyl ether
washThe organic layer was washed with water
dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
customThe residue was purified with silica gel column chromatography (ethyl acetate ether: hexane=1:9)

Quellen und Nachweise

ORD-Eintrag: ord-c74a8cac6b1e46f7bf1fc4135f11063b
Quelldatensatz: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07273878B2

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