Sodium methanethiolate → HCID 54276775, compound

HRID 1696747Notes

Reaction equation

HRID 1696747 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([Br:11])[N:3]=1.[CH3:12][S-:13].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([S:13][CH3:12])[CH:5]=[C:4]([Br:11])[N:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 160387482,6-Dibromo-4-nitropyridine

Product 1

HCID 54276775HCID 54276775, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dibromo-4-nitro-pyridine (CAS 175422-04-5, 10.0 g, 35.5 mmol) in 60 mL of DMF was added at −10° C. sodium methanethiolate (2.61 g, 1.05 eq.) and the mixture stirred for 45 Min. at this temperature and for another 2 h at 0° C. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=97/3), yielded 8.55 g of the title compound as off-white crystals.

Workup

  1. additionPouring
  2. extractionice, twofold extraction with AcOEt
  3. washwashing with water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-1b732ba545f14fdc99dde1ea72e1c2b3
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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