Ethyl (chloroformyl)acetate → Ethyl thiazole-5-carboxylate

HRID 1180122Notes

Reaction equation

HRID 1180122 reaction equation
[CH:1]([NH2:3])=[S:2].Cl[CH:5]([CH:11]=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7]>CC(C)=O>[S:2]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][N:3]=[CH:1]1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 3005587Methanethioamide

Product 1

HCID 459108Ethyl thiazole-5-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a round bottom flask was added 250 mL of dry acetone, 7.5 g (0.123 mol) of thioformamide, and 18.54 g (0.123 mol) of ethyl 2-chloro-2-formylacetate. The reaction was heated at reflux for 2 hours. The solvent was removed in vacuo, and the residue was purified by chromatography (SiO2, 6 cm o.d. column, 100% CHCl3, Rf=0.25) to provide 11.6 g (60%) of the desired compound as a light yellow oil. NMR (CDCl3 δ 1.39 (t, J=7 Hz, 3H), 4.38 (q, J=7 Hz, 2H), 8.50 (s, 1H), 8.95 (s, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by chromatography (SiO2, 6 cm o.d

Sources & evidence

ORD record
ord-7a4fe8b73a724193bc18f452839a1d63
Source dataset
uspto-grants-2007_10
Patent number
US07279582B2

Reaction notes

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