Sodium Chloride → HCID 23079405, compound

HRID 1392210Notes

Reaction equation

HRID 1392210 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][O:9][CH2:10][CH3:11])[N:3]=1.[CH3:12][C:13]1([CH3:20])[O:17][CH:16]([CH2:18][OH:19])[CH2:15][O:14]1.[H-].[Na+].[Cl-].[Na+]>C(OC)(C)(C)C.CN(C)C=O>[CH3:12][C:13]1([CH3:20])[O:17][CH:16]([CH2:18][O:19][C:2]2[S:6][N:5]=[C:4]([S:7][CH2:8][O:9][CH2:10][CH3:11])[N:3]=2)[CH2:15][O:14]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7528SolketalHCID 24758Sodium hydrideHCID 12151393HCID 12151393, compound

Product 1

HCID 23079405HCID 23079405, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To 3 g of N,N-dimethylformamide, 300 mg of 5-chloro-3-ethoxymethylthio-1,2,4-thiadiazole and 188 mg of 2,2-dimethyl-1,3-dioxolane-4-methanol were dissolved, and added 62 mg of sodium hydride (60% in oil) at about 0° C., followed by stirring at about 0° C. for 30 minutes and standing at room tempareture for about 1 day. Then, to the reaction mixture, t-butylmethylether and saturated sodium chloride aqueous solution were added, and separeted to two layers. The organic layer was dried by anhydrous sodium salfate, and concentrated. The residue obtaind was subjected to column chromatography to obtain 330 mg of 5-(2,2-dimethyl-1,3-dioxolane-4-yl)methoxy-3-ethoxymethylthio-1,2,4-thiadiazole.

Workup

  1. waitstanding at room tempareture for about 1 day
  2. dry with materialThe organic layer was dried by anhydrous sodium salfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-95c6e5ec341842d7be030f1f1fb5f0ef
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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