Sodium Bicarbonate → 8-(4-(4-Methoxyphenyl)-5-(p-tolyl)thiazol-2-yl)-1,4-dioxaspiro[4.5]decane

HRID 888294

Reaktionsgleichung

Reaktionsgleichung von HRID 888294
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11](=[S:13])[NH2:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Br[CH:15]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=O.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[N:12]=[C:11]([CH:8]3[CH2:9][CH2:10][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:6][CH2:7]3)[S:13][C:15]=2[C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 463987762-Bromo-1-(4-methoxyphenyl)-2-(p-tolyl)ethanoneHCID 579299251,4-Dioxaspiro[4.5]decane-8-carbothioamide

Produkt 1

HCID 672963928-(4-(4-Methoxyphenyl)-5-(p-tolyl)thiazol-2-yl)-1,4-dioxaspiro[4.5]decaneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1,4-dioxaspiro[4.5]decane-8-carbothioamide (Reference Example 94) (389 mg, 1.93 mmol) and 2-bromo-1-(4-methoxyphenyl)-2-(p-tolyl)ethanone (588 mg, 1.84 mmol) in acetonitrile (9.2 mL) was stirred at room temperature for 4 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (630 mg, 1.49 mmol, 81%) as a colorless amorphous product.

Aufarbeitung

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0333eb0cc5ee4d47b94de08d125eb4dd
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247569B2

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