Iodine → HCID 68276422, compound

HRID 334396Notes

Reaction equation

HRID 334396 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-7beaa1dcb2874e5780dc731de167aab7
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

Loading…