Potassium Carbonate → Ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate

HRID 2205084Notes

Reaction equation

HRID 2205084 reaction equation
Br.[CH3:2][C:3]1[S:7][C:6]2=[N:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:5]2[CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:2][C:3]1[S:7][C:6]2=[N:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:5]2[CH:4]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 70817978Ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate hydrobromide

Product 1

HCID 70817425Ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetateYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl (2-methylimidazo[2,1-b][1,3]thiazol-6-yl)acetate hydrobromide (226 g, 0.74 mol) was dissolved in water (350 mL) and the solution was adjusted to pH 7 by addition of potassium carbonate (51.0 g, 0.37 mol). The aqueous solution was extracted with methylene chloride (300 mL) and the organic phase was washed with brine (150 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give ethyl (2-methylimidazo[2,1-b][1,3]thiazol-6-yl)acetate as a brown oil (151.3 g).

Workup

  1. extractionThe aqueous solution was extracted with methylene chloride (300 mL)
  2. washthe organic phase was washed with brine (150 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-724238e37e43407da29e572879ecbebc
Source dataset
uspto-grants-2016_06
Patent number
US09370516B2

Reaction notes

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