Sodium methanethiolate → HCID 59526020, compound

HRID 385919Notes

Reaction equation

HRID 385919 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[N:3]=1.[CH3:10][S-:11].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][S:11][CH3:10])[N:3]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 59526020HCID 59526020, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (0.20 g, 0.80 mmol) and sodium thiomethoxide (0.072 g, 1.04 mmol) were taken up in DMF (12.1 mL) heated at 80° C. for 3 hours. The reaction was then cooled to ambient temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography to yield the title compound. 1H NMR (600 MHz, CDCl3): 7.53 (t, J=9.0 Hz, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.36 (d, J=9.0 Hz, 1H), 3.77 (s, 2H), 2.08 (2, 3H).

Workup

  1. temperatureThe reaction was then cooled to ambient temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ff1142a19d8041b9b77af9852b38cb5b
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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