Hydrochloric Acid → HCID 21928110, compound

HRID 488905Notes

Reaction equation

HRID 488905 reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:5][C:6](=[O:14])[CH:7]=[C:8]([S:12][CH3:13])[C:9]=1[C:10]#[N:11].Br[CH2:16][C:17]([NH2:19])=[O:18].Cl>CN(C=O)C>[C:10]([C:9]1[C:8]([S:12][CH3:13])=[CH:7][C:6](=[O:14])[NH:5][C:4]=1[S:3][CH2:16][C:17]([NH2:19])=[O:18])#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 153952271,6-Dihydro-2-mercapto-4-(methylthio)-6-oxo-3-pyridinecarbonitrile

Product 1

HCID 21928110HCID 21928110, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (2.60 g, 65.0 mmol) was added to a solution of 2-mercapto-4-methylsulfanyl-6-oxo-1,6-dihydro-pyridine-3-carbonitrile (12.5 g, 63 mmol) in DMF (300 mL) cooled in an ice water bath. The mixture was stirred for 30 min then 2-bromoacetamide was added (8.80 g, 64 mmol) as a solid in one portion. The mixture was slowly warmed to room temperature and stirred for 15 h then poured onto ice water. The mixture was acidified with 2N HCl, filtered, and the resulting precipitate was washed with diethyl ether then hexanes to provide 11.3 g (70%) of 2-(3-cyano-4-methylsulfanyl-6-oxo-1,6-dihydro-pyridin-2-ylsulfanyl)-acetamide as a tan solid.

Workup

  1. temperaturecooled in an ice water bath
  2. stirringstirred for 15 h
  3. additionthen poured onto ice water
  4. filtrationfiltered
  5. washthe resulting precipitate was washed with diethyl ether

Sources & evidence

ORD record
ord-423642c4937e4fe49b132128404dde1e
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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