Ethyl Acetate → 6-Amino-5-iodo-2-(methylsulfinyl)nicotinonitrile

HRID 1487368Notes

Reaction equation

HRID 1487368 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[NH2:12][C:13]1[C:20]([I:21])=[CH:19][C:16]([C:17]#[N:18])=[C:15]([S:22][CH3:23])[N:14]=1.C(OCC)(=O)C>ClCCl>[NH2:12][C:13]1[C:20]([I:21])=[CH:19][C:16]([C:17]#[N:18])=[C:15]([S:22]([CH3:23])=[O:9])[N:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 68276422HCID 68276422, compound

Product 1

HCID 682764766-Amino-5-iodo-2-(methylsulfinyl)nicotinonitrileYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.77 g (1.1 eq) of 70% 3-chloroperbenzoic acid is added to a solution of 1.89 g (6.51 mmol) of 6-amino-5-iodo-2-(methylthio)nicotinonitrile in 60 ml of dichloromethane. The reaction medium is stirred at room temperature for 1 hour. Ethyl acetate is added and the organic phase is washed with saturated sodium bicarbonate solution, dried on magnesium sulfate, filtered and evaporated to yield 1.5 g (75%) of 6-amino-5-iodo-2-(methylsulfinyl)nicotinonitrile in the form of a white powder which may also contain 6-amino-5-iodo-2-(methylsulfonyl)nicotinonitrile in small proportions (<20%). If necessary, the mixture is used as-is in the following steps.

Workup

  1. washthe organic phase is washed with saturated sodium bicarbonate solution
  2. customdried on magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-68a782b162a4456b84f1458f66572b74
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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