Sodium Chloride → HCID 23079417, compound

HRID 1392207Notes

Reaction equation

HRID 1392207 reaction equation
[CH3:1][S:2][C:3]1[N:7]=[C:6](Cl)[S:5][N:4]=1.[CH2:9]1[O:13][CH2:12][O:11][CH:10]1[CH2:14][OH:15].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[O:13]1[CH2:9][CH:10]([CH2:14][O:15][C:6]2[S:5][N:4]=[C:3]([S:2][CH3:1])[N:7]=2)[O:11][CH2:12]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 216181,3-Dioxolane-4-methanolHCID 24758Sodium hydrideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 23079417HCID 23079417, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 10 ml of N,N-dimethylformamide, 835 mg of 3-methylthio-5-chloro-1,2,4-thiadiazole and 520 mg of glycerol formal were dissolved, and added 204 mg of sodium hydride (60% in oil) at about 0° C., followed by stirring at about 0° C. for 20 minutes and at room temperature for 30 minutes. Then, the reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with tert-butylmethylether. After the organic layer was dried by anhyrous sodium salfate, the organic layer was concentrated, and the residue obtaind was subjected to silica gel column chromatography (hexane:ethyl acetate=20:1), followed preparative HPLC to obtain 250 mg of 5-(1,3-dioxolane-4-yl)methoxy-3-methylthio-1,2,4-thiadiazole.

Workup

  1. extractionextracted with tert-butylmethylether
  2. dry with materialAfter the organic layer was dried by anhyrous sodium salfate
  3. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-e3680bdc53d5448aabb88f7515b446a8
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

Loading…