Pyridine → HCID 18772052, compound

HRID 460190Notes

Reaction equation

HRID 460190 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[S:10])[NH2:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.Br[CH2:13][C:14](=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].N1C=CC=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[S:10][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:9]=2)[CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 66144Ethyl bromopyruvateHCID 27818592,6-dichloropyridine-4-carbothioamide

Product 1

HCID 18772052HCID 18772052, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,6-Dichloropyridine-4-thiocarboxamide (1.0 g, 4.83 mmol) was dissolved in dry 1,4-dioxane followed by adding ethyl bromopyruvate (0.9 mL, 7.24 mmol) and pyridine (0.4 mL, 4.83 mmol). The resulting mixture was heated to reflux under N2 for 5 h. After cooling to RT, solvent was removed. The residue was extracted with CHCl3. The organic layer was washed with H2O and brine, dried over MgSO4, and concentrated to give a brownish solid. This crude was purified by chromatography on silica gel. Elution with hexane:acetone (90:10) gave a title compound as yellow solid. MS m/z: 303 (M+H). Calc'd. for C11H8Cl2N2O2S-303.16.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux under N2 for 5 h
  3. customsolvent was removed
  4. extractionThe residue was extracted with CHCl3
  5. washThe organic layer was washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give a brownish solid
  9. customThis crude was purified by chromatography on silica gel
  10. washElution with hexane:acetone (90:10)

Sources & evidence

ORD record
ord-b0e3719767fa48b58aeb12e2ec3ebe5c
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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