2-Pyridinamine, 5-iodo- → HCID 28412369, compound

HRID 614845Notes

Reaction equation

HRID 614845 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[SH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C[O-].[Na+]>[Cu].CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 885792-Pyridinamine, 5-iodo-HCID 10942334Sodium MethoxideHCID 178418616HCID 178418616, compound

Product 1

HCID 28412369HCID 28412369, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

11.0 G. (0.05 moles) of 2-amino-5-iodo pyridine, 6.1 g. (0.055 moles) of 2-mercapto pyridine, 2.97 g. (0.055 moles) of sodium methoxide and 1.0 g. of copper powder are combined in 200 ml. of methanol and heated at 150° C. for 12 hours in a glass lined bomb. The reaction mixture is filtered and the filtrate evaporated to dryness in vacuo. The residue is dissolved in 300 ml. of methylenechloride and washed 5 times with 2.5 N sodium hydroxide and 3 times with saturated sodium chloride solution. The methylene chloride is dried over magnesium sulfate, and evaporated to dryness. The residue is dissolved in boiling methanol, treated with decolorizing carbon, filtered and evaporated to dryness affording 2-amino-5-(2-pyridylthio) pyridine, m.p. 121° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate evaporated to dryness in vacuo
  3. dissolutionThe residue is dissolved in 300 ml
  4. washof methylenechloride and washed 5 times with 2.5 N sodium hydroxide and 3 times with saturated sodium chloride solution
  5. dry with materialThe methylene chloride is dried over magnesium sulfate
  6. customevaporated to dryness
  7. dissolutionThe residue is dissolved
  8. additiontreated with decolorizing carbon
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-7728afb6d73d44f6a97421fe6a6d8faf
Source dataset
uspto-grants-1979_03
Patent number
US04146642

Reaction notes

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