Iodine → HCID 68276422, compound

HRID 1487367Notes

Reaction equation

HRID 1487367 reaction equation
[I:1]I.[NH2:3][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]>[NH2:3][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 682765271392149-89-1

Product 1

HCID 68276422HCID 68276422, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

3.75 g (1.5 eq) of silver sulfate and 2.85 g (1.4 eq) of iodine are added successively to a solution of 1.32 g (8.02 mmol) of 6-amino-2-(methylthio)nicotinonitrile in 65 ml of ethanol. The reaction medium is stirred at room temperature for 3 hours. The solid is filtered and the residue rinsed thoroughly with methanol. The filtrate is evaporated and redissolved in ethyl acetate. The organic phase is washed with water three times, dried on magnesium sulfate and evaporated to yield 1.89 g (81%) of 6-amino-5-iodo-2-(methylthio)nicotinonitrile in the form of a brown powder.

Workup

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

Sources & evidence

ORD record
ord-ca39edab064d4d679183b15ace45b9a9
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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