Sodium hydride → HCID 21928110, compound

HRID 1243793Notes

Reaction equation

HRID 1243793 reaction equation
[SH:1][C:2]1[NH:3][C:4](=[O:12])[CH:5]=[C:6]([S:10][CH3:11])[C:7]=1[C:8]#[N:9].[H-].[Na+].Br[CH2:16][C:17]([NH2:19])=[O:18]>CN(C=O)C>[C:8]([C:7]1[C:6]([S:10][CH3:11])=[CH:5][C:4](=[O:12])[NH:3][C:2]=1[S:1][CH2:16][C:17]([NH2:19])=[O:18])#[N:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 153952271,6-Dihydro-2-mercapto-4-(methylthio)-6-oxo-3-pyridinecarbonitrile

Product 1

HCID 21928110HCID 21928110, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the above 2-mercapto-4-methylsulfanyl-6-oxo-1,6-dihydro-pyridine-3-carbonitrile (12.5 g, 63.0 mmol) in DMF (300 mL), cooled to 0° C., was added sodium hydride (2.60 g, 65.0 mmol) as a 60% dispersion in mineral oil. The mixture was stirred at 0° C. for 30 min then 2-bromoacetamide (8.80 g, 63.8 mmol) was added as a solid in one portion. The mixture was allowed to slowly warm to room temperature and stirred for 15 h. The mixture poured into ice—H2O and stirred until all of the ice had melted, during which time a solid precipitated from solution. The mixture was acidified with 2N HCl then cooled to 0° C. and the solid collected by filtration. The material was washed with Et2O followed by hexanes to provide 11.2 g (69.9%) of 2-(3-cyano-4-methylsulfanyl-6-oxo-1,6-dihydro-pyridin-2-ylsulfanyl)-acetamide as a tan solid.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringstirred for 15 h
  3. customprecipitated from solution
  4. temperaturethen cooled to 0° C.
  5. filtrationthe solid collected by filtration
  6. washThe material was washed with Et2O

Sources & evidence

ORD record
ord-0dcede120d9442bcad3ffdd179b7006c
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

Loading…