Hydrochloric Acid → Ethyl 2-formyl-1,3-thiazole-4-carboxylate

HRID 907380Notes

Reaction equation

HRID 907380 reaction equation
C([O:3][CH:4](OCC)[C:5]1[S:6][CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:9]=1)C.Cl>CC(C)=O>[CH:4]([C:5]1[S:6][CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16220290Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

Product 1

HCID 11355896Ethyl 2-formyl-1,3-thiazole-4-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 2-(diethoxymethyl)-1,3-thiazole-4-carboxylate (1.34 g, 5.17 mmol; see step (iv) above) was taken up in acetone (100 mL) and a solution of 1N HCl (12.8 mL) was then added. The solution was refluxed for 45 min and the solvent removed under reduced pressure. The residue was then dissolved in ethyl acetate (40 mL) and extracted with saturated NaHCO3 solution (2×40 mL) and brine (2×40 mL). The organic fraction was then dried (MgSO4), filtered and the solvent removed under reduced pressure to yield the sub-title compound as a light brown solid (0.937 g, 98%).

Workup

  1. temperatureThe solution was refluxed for 45 min
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was then dissolved in ethyl acetate (40 mL)
  4. extractionextracted with saturated NaHCO3 solution (2×40 mL) and brine (2×40 mL)
  5. dry with materialThe organic fraction was then dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-11a31948ecc140d4be71da7899c446b1
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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