Ethyl Acetate → HCID 68276344, compound

HRID 334392Notes

Reaction equation

HRID 334392 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[I:12][C:13]1[C:14]([O:23][CH3:24])=[N:15][C:16]([S:21][CH3:22])=[C:17]([CH:20]=1)[C:18]#[N:19].C(OCC)(=O)C>ClCCl>[I:12][C:13]1[C:14]([O:23][CH3:24])=[N:15][C:16]([S:21]([CH3:22])=[O:9])=[C:17]([CH:20]=1)[C:18]#[N:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 68276426HCID 68276426, compound

Product 1

HCID 68276344HCID 68276344, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.42 g (1.1 eq) of 70% 3-chloroperbenzoic acid is added to a solution of 1.6 g (5.23 mmol) of 5-iodo-6-methoxy-2-(methylthio)nicotinonitrile in 20 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 1.63 g (97%) of 5-iodo-6-methoxy-2-(methylsulfinyl)nicotinonitrile in the form of a white powder which may also contain 5-iodo-6-methoxy-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-fe75c7c768bd41c58182fb8016be2019
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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