Iodine → HCID 178503563, compound

HRID 1487361Notes

Reaction equation

HRID 1487361 reaction equation
[I:1]I.[OH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([S:12][CH3:13])[N:5]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[OH:3][C:4]1[C:11]([I:1])=[CH:10][C:7]([C:8]#[N:9])=[C:6]([S:12][CH3:13])[N:5]=1

Participants

5

Reactant 2

HCID 807IodineHCID 178503531HCID 178503531, compound

Product 1

HCID 178503563HCID 178503563, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

6 g (1.6 eq) of silver sulfate and 4.58 g (1.5 eq) of iodine are added successively to a solution of 2 g (12 mmol) of 6-hydroxy-2-(methylthio)nicotinonitrile in 200 ml of ethanol. The reaction medium is stirred at room temperature for 2 hours. The solid is filtered and the residue rinsed thoroughly with methanol. The filtrate is evaporated and then taken up in ethyl acetate. The organic phase is washed with water three times, dried on magnesium sulfate and evaporated to yield 3.18 g (90%) of 6-hydroxy-5-iodo-2-(methylthio)nicotinonitrile in the form of a yellow powder.

Workup

  1. filtrationThe solid is filtered
  2. washthe residue rinsed thoroughly with methanol
  3. customThe filtrate is evaporated
  4. washThe organic phase is washed with water three times
  5. customdried on magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f10d0fa607e1427caddceec7135719a9
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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