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

HRID 1392209Notes

Reaction equation

HRID 1392209 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10]1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][O:15][C:2]2[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=2)=[CH:10]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 123570Thiophene-3-methanolHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 230794035-(3-Thienyl)methoxy-3-methylthio-1,2,4-thiadiazoleYield 102.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 4 ml of N,N-dimethylformamide, 0.334 g of 5-chloro-3-methylthio-1,2,4-thiadiazole and 228 mg of 3-thiophenemethanol were dissolved, and added 0.084 g of sodium hydride (60% in oil) at about 0° C., followed by stirring at about 0° C. for 0.5 hours and at room temperature for 4 hours. Then, the reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with tert-butylmethylether. The organic layer was concentrated, and the residue obtaind was subjected to silica gel column chromatography to obtain 500 mg of 5-(3-thienyl)methoxy-3-methylthio-1,2,4-thiadiazole.

Workup

  1. extractionextracted with tert-butylmethylether
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-73818ef89efe493fb70df0fb6b91ee99
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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