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

HRID 82307Notes

Reaction equation

HRID 82307 reaction equation
C([O-])([O-])=O.[K+].[K+].Br.[CH3:8][C:9]1[S:13][C:12]2=[N:14][C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][N:11]2[CH:10]=1>O>[CH3:8][C:9]1[S:13][C:12]2=[N:14][C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][N:11]2[CH:10]=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 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4-bromo-3-oxobutanoate (92 g, 0.35 mol) was added to a solution of 5-methylthiazol-2-amine (40 g, 0.35 mol) in acetone (400 mL). The mixture was left to stand overnight and then evaporated to give 2-amino-3-(4-ethoxy-2,4-dioxobutyl)-5-methylthiazol-3-ium bromide in 82% yield, 101 g. 2-amino-3-(4-ethoxy-2,4-dioxobutyl)-5-methylthiazol-3-ium bromide (101 g, 0.28 mol) was then refluxed in ethanol (250 mL) for 2 hours. The solvent was then evaporated to give ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate hydrobromide as yellow crystals in 97% yield, 85 g. Solid K2CO3 was added to a solution of ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate hydrobromide (85 g, 0.28 mol) in water (300 mL) to pH ˜8. The product was extracted with chloroform (3×100 mL), and the combined extracts were dried over Na2SO4 and evaporated to give ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate in 84% yield 52 g. Ethyl 2-(2-methylimidazo[2,1-b]thiazol-6-yl)acetate (52 g, 0.23 mol) was refluxed in 10% aqueous HCl (150 mL) for 2 hours. The solution was evaporated to dryness to give the title compound as brown crystals in 59% yield 32.3 g; m/z 197 [M+H]+.

Workup

  1. extractionThe product was extracted with chloroform (3×100 mL)
  2. dry with materialthe combined extracts were dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-456c51de56384e56a561aa86b26e61bc
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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