Ethyl 4-chloroacetoacetate → Ethyl (2-methyl-1,3-thiazol-4-yl)acetate

HRID 915676Notes

Reaction equation

HRID 915676 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].[CH2:5]([O:7][C:8](=[O:14])[CH2:9][C:10]([CH2:12]Cl)=O)[CH3:6]>C(O)C>[CH2:5]([O:7][C:8](=[O:14])[CH2:9][C:10]1[N:4]=[C:1]([CH3:2])[S:3][CH:12]=1)[CH3:6]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 2723949Thioacetamide

Product 1

HCID 854815Ethyl (2-methyl-1,3-thiazol-4-yl)acetateYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepare a solution of thioacetamide (10 g, 133 mmol) in ethanol (75 mL). Add ethyl-4-chloroacetoacetate (16.5 mL, 122 mmol). Stir the reaction overnight at 50° C. and then concentrate in vacuo. Dissolve the resulting oil in water (75 mL) and extract with diethyl ether (3×50 mL). Extract the aqueous layer with CHCl3 (3×50 mL). Wash the combined organic layers with brine (50 mL), dry (Na2SO4), filter, and concentrate in vacuo to afford (2-methylthiazol-4-yl)acetic acid ethyl ester (17 g) as a solid. 1H NMR (CDCl3) δ 7.02 (s, 1H), 4.15-4.25 (m, 2H), 3.79 (s, 2H), 2.71 (s, 3H), 1.25 (t, J=7 Hz, 3H).

Workup

  1. customthe reaction overnight at 50° C.
  2. concentrationconcentrate in vacuo
  3. dissolutionDissolve the resulting oil in water (75 mL)
  4. extractionextract with diethyl ether (3×50 mL)
  5. extractionExtract the aqueous layer with CHCl3 (3×50 mL)
  6. washWash the combined organic layers with brine (50 mL)
  7. dry with materialdry (Na2SO4)
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0344de82e2114c239f1d337ee1aacec8
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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