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

HRID 888294

Reaction equation

HRID 888294 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0333eb0cc5ee4d47b94de08d125eb4dd
Source dataset
uspto-grants-2012_08
Patent number
US08247569B2

Linked notes

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