Ethyl Thioglycolate → HCID 59525890, compound

HRID 385917Notes

Reaction equation

HRID 385917 reaction equation
[H-].[Na+].[SH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]Br)[N:12]=1>O1CCCC1.O>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][S:3][CH2:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([Br:10])[N:12]=1)[CH3:9]

Participants

6

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 59525890HCID 59525890, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.48 g, 11.96 mmol) was suspended in tetrahydrofuran (52.4 mL) and cooled to 0° C. Ethyl mercaptoacetate (0.48 mg, 3.99 mmol) was added and the solution was stirred for 30 minutes at 0° C. 2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (1.0 g, 3.99 mmol) was added and the solution was allowed to stir until completion. The reaction mixture was then diluted with water and extracted with ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered, concentrated, and purified by silica gel chromatography to yield the title compound.

Workup

  1. stirringto stir until completion
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f1fa9b4f8b1f4a4d9c62d1a140ef9ed4
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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