Dimethyl Sulfoxide → 5-(Methylsulfonyl)pyridine-2-carbonitrile

HRID 1517473Notes

Reaction equation

HRID 1517473 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:10][S:11]([O-:13])=[O:12].[Na+].CS(C)=O>O>[CH3:10][S:11]([C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8171545-Bromopyridine-2-carbonitrileHCID 2733271Sodium methanesulfinate

Product 1

HCID 591699295-(Methylsulfonyl)pyridine-2-carbonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Bromo-2-cyanopyridine (38.0 kg 1.0 mol eq, limiting reagent) and sodium methane sulfinate (29.68 kg, 1.4 mol eq) were charged followed by DMSO (228 L, 6 rel vol). The reaction was heated to 100° C.-105° C. and stirred until reaction complete as judged by HPLC analysis. After cooling, the reaction mixture was added to preheated water (356 L, 9.4 rel vol). After cooling and stirring, the product was isolated by filtration. The solid was washed with water (456 L, 12 rel vol) and dried to constant weight to yield the title compound (33 kg, 18.1 mol, 87%).

Workup

  1. additionwere charged
  2. temperatureThe reaction was heated to 100° C.-105° C.
  3. temperatureAfter cooling
  4. temperatureAfter cooling
  5. stirringstirring
  6. customthe product was isolated by filtration
  7. washThe solid was washed with water (456 L, 12 rel vol)
  8. customdried to constant weight

Sources & evidence

ORD record
ord-5fd7497238304b71aa6e5a0012b311a3
Source dataset
uspto-grants-2012_07
Patent number
US08232296B2

Reaction notes

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