Sodium Chloride → HCID 23032430, compound

HRID 917326Notes

Reaction equation

HRID 917326 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].Cl[C:12]1[S:16][N:15]=[C:14]([S:17][CH3:18])[N:13]=1.[Cl-].[Na+]>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:12]1[S:16][N:15]=[C:14]([S:17][CH3:18])[N:13]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11474PiconolHCID 24758Sodium hydrideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 23032430HCID 23032430, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into 2 ml of N,N-dimethylformamide was dissolved 218 mg of 2-pyridylmethanol, 84 mg of sodium hydride (60% in oil) was added thereto under ice-cooling. After stirring for 15 minutes, a solution of 334 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole in 2 ml of N,N-dimethylformamide was added dropwise into the mixture and the reaction mixture was stirred for 0.5 hour under ice-cooling and for 2 hours at room temperature. The reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 30 mg of 5-(2-pyridylmethyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (19)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringthe reaction mixture was stirred for 0.5 hour under ice-
  4. extractionextracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated
  6. customthe residue obtained

Sources & evidence

ORD record
ord-1071ac6985204e44839eb2fa9ab8824b
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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