Ethanol → HCID 86702822, compound

HRID 1850063Notes

Reaction equation

HRID 1850063 reaction equation
Cl[CH2:2][C:3]([CH2:5]Cl)=O.[NH2:7][C:8]1[S:9][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:12]=1.[CH3:20][CH2:21][OH:22]>>[CH2:21]([O:22][CH2:5][C:3]1[N:7]=[C:8]2[N:12]([CH:2]=1)[CH:11]=[C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:9]2)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 107931,3-DichloroacetoneHCID 86702821HCID 86702821, compound

Product 1

HCID 86702822HCID 86702822, compound

Conditions

Temperature
80 °C

Procedure

1,3-Dichloroacetone (0.252 g, 2 mmol) was added to a solution of (E)-ethyl 3-(2-aminothiazol-5-yl)acrylate (0.199 g, 1 mmol) in EtOH (5 mL). The solution was heated at 80° C. overnight in a closed vial. The reaction mixture was then evaporated and the residue was treated with a saturated NaHCO3 solution (20 mL). It was extracted with EtOAc (30 mL). The organic layer was separated, dried over Na2SO4, filtered and evaporated. The crude was purified by silica gel column chromatography (50-100% gradient of EtOAc in Hexanes) to provide pure (E)-ethyl 3-(6-(ethoxymethyl)imidazo[2,1-b]thiazol-2-yl)acrylate (0.080 g) as a tan solid. ES+(M+H)+281.

Workup

  1. customThe reaction mixture was then evaporated
  2. additionthe residue was treated with a saturated NaHCO3 solution (20 mL)
  3. extractionIt was extracted with EtOAc (30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by silica gel column chromatography (50-100% gradient of EtOAc in Hexanes)

Sources & evidence

ORD record
ord-29982206fc754ff9bb83a36936ddcff6
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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