Sodium Chloride → 5-(4-Pyridylmethyloxy)-3-methylthio-1,2,4-thiadiazole

HRID 917335Notes

Reaction equation

HRID 917335 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.[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][C:4]([CH2:7][O:8][C:12]2[S:16][N:15]=[C:14]([S:17][CH3:18])[N:13]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 114724-HydroxymethylpyridineHCID 24758Sodium hydrideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 121513895-(4-Pyridylmethyloxy)-3-methylthio-1,2,4-thiadiazoleYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into 4 g of N,N-dimethylformamide was dissolved 218 mg of 4-pyridinemethanol, 96 mg of sodium hydride (60% in oil) was added thereto at room temperature. After stirring for 30 minutes, a solution of 334 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole in 1 g of N,N-dimethylformamide was added dropwise into the mixture and the reaction mixture was stirred for 4 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 260 mg of 5-(4-pyridylmethyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (34)).

Workup

  1. additionwas added
  2. customat room temperature
  3. stirringthe reaction mixture was stirred for 4 hours at room temperature
  4. extractionextracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated
  6. customthe residue obtained

Sources & evidence

ORD record
ord-46688fcd0cd64a59b18c09ff254f94ed
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

Loading…