Iodine → HCID 178503563, compound

HRID 1048754Notes

Reaction equation

HRID 1048754 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-57539934857c4e78a45be677c930a753
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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