5-Chloro-2-nitropyridine → 5-(Methylthio)-2-nitropyridine

HRID 1658368Notes

Reaction equation

HRID 1658368 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:11][S-:12].[Na+]>C(O)C>[CH3:11][S:12][C:2]1[CH:3]=[CH:4][C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 2598065-Chloro-2-nitropyridineHCID 4378561Sodium methanethiolate2×

Product 1

HCID 220361825-(Methylthio)-2-nitropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-2-nitropyridine (8.0 grams) was added to a solution of 2.5 grams of sodium methanethiolate in 100 milliliters of ethanol at a temperature of 0°C. to which solution excess sodium methanethiolate was added portionwise. The resulting reaction mixture was then heated to reflux and refluxed for 15 hours with constant stirring. At the end of the 15 hours, the reaction mixture was filtered and allowed to concentrate to 75 milliliters. The reaction mixture was then permitted to cool and filtered again, yielding the desired 5-(methylthio)-2-nitropyridine; it was recrystallized from ethanol, m.p., 100.5-02.5°C.

Workup

  1. additionwas added portionwise
  2. customThe resulting reaction mixture
  3. temperaturewas then heated
  4. temperatureto reflux
  5. temperaturerefluxed for 15 hours with constant stirring
  6. filtrationAt the end of the 15 hours, the reaction mixture was filtered
  7. concentrationto concentrate to 75 milliliters
  8. temperatureto cool
  9. filtrationfiltered again

Sources & evidence

ORD record
ord-ca938a7fb7674bce8011cc50ec36a256
Source dataset
uspto-grants-1976_06
Patent number
US03963734

Reaction notes

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