Sodium Chloride → HCID 23079418, compound

HRID 1392211Notes

Reaction equation

HRID 1392211 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH3:17][C:18]1([CH3:25])[O:22][CH:21]([CH2:23][OH:24])[CH2:20][O:19]1.[H-].[Na+].[Cl-].[Na+]>C(OC)(C)(C)C.CN(C)C=O>[CH3:17][C:18]1([CH3:25])[O:22][CH:21]([CH2:23][O:24][C:2]2[S:6][N:5]=[C:4]([S:7][CH2:8][O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:3]=2)[CH2:20][O:19]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7528SolketalHCID 24758Sodium hydrideHCID 23032434HCID 23032434, compound

Product 1

HCID 23079418HCID 23079418, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To 3 g of N,N-dimethylformamide, 350 mg of 5-chloro-3-benzyloxymethylthio-1,2,4-thiadiazole and 169 mg of 2,2-dimethyl-1,3-dioxolane-4-methanol were dissolved, and added 56 mg of sodium hydride (60% in oil) at about 0° C., followed by stirring at same tempareture for 2 hours. 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-benzyloxymethylthio-1,2,4-thiadiazole.

Workup

  1. dry with materialThe organic layer was dried by anhydrous sodium salfate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6b37be932fb4475bbadb4a0677efd115
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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