Dimethylformamide → 6,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinate

HRID 917359

Reaktionsgleichung

CN(C)C=O.CS([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])(=O)=O.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][N:22]=1.C(=O)([O-])O.[Na+]>O>[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])=[O:26])=[CH:23][N:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To 7 ml of N,N-dimethylformamide were dissolved 0.92 g (4.0 mmol) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate and 0.72 g (5.2 mmol) of 6-aminonicotinic acid, followed by the addition of 1.30 g (16 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with ethyl acetate. 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:hexane=1:1) to obtain 0.85 g (yield: 78%) of 6,6-difluoro-5-methyl-5-hexenyl 6-aminonicotinate.

Aufarbeitung

customThe reaction liquid
extractionextracted with ethyl acetate
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:hexane=1:1)

Quellen und Nachweise

ORD-Eintrag: ord-d887f99e52204fbf8dc28b0181e8ef2c
Quelldatensatz: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07273878B2

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