2-Pyridinecarboxamide → Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylate

HRID 643088

Reaction equation

HRID 643088 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH2:9])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:19])=CC=1.Br[CH2:33][C:34](=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36]>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:19][CH:33]=[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:9]=1

Participants

5

Reactant 3

HCID 150702-PyridinecarboxamideHCID 66144Ethyl bromopyruvateHCID 87949Lawesson's reagent

Product 1

HCID 10082761Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylateYield 33%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

2-Picolinamide (3.1 g, 25.4 mmol) was dissolved in toluene (25 mL) and treated with Lawesson's Reagent (5.1 g, 0.5 equivalents). The reaction was heated to 85° C. and stirred for 48 hrs. The reaction was quenched with water and extracted and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and the solvent was removed by evaporation. This material was dissolved in ethanol (50 mL) and treated with ethyl bromopyruvate (3 mL, about 1 equivalent) and powdered 3 A molecular sieves (10 g). The reaction was refluxed for 16 hrs. The reaction was then filtered and the solvent was removed by evaporation. The material was dissolved in ethyl acetate, washed with a saturated solution of sodium bicarbonate, washed with brine, and dried over magnesium sulfate. The reaction was filtered and the solvents were removed by evaporation. This material was purified using dichloromethane:ethyl acetate (3:1) to give 1.98 g of the title compound (33%).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed by evaporation
  8. dissolutionThis material was dissolved in ethanol (50 mL)
  9. temperatureThe reaction was refluxed for 16 hrs
  10. filtrationThe reaction was then filtered
  11. customthe solvent was removed by evaporation
  12. dissolutionThe material was dissolved in ethyl acetate
  13. washwashed with a saturated solution of sodium bicarbonate
  14. washwashed with brine
  15. dry with materialdried over magnesium sulfate
  16. filtrationThe reaction was filtered
  17. customthe solvents were removed by evaporation
  18. customThis material was purified

Sources & evidence

ORD record
ord-e78f54882920464896b2e91c83cd9999
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Linked notes

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