Sodium Chloride → HCID 23079426, compound

HRID 1392204Notes

Reaction equation

HRID 1392204 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[N:3]=1.[CH3:16][C:17]1([CH3:24])[O:21][CH:20]([CH2:22][OH:23])[CH2:19][O:18]1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH3:16][C:17]1([CH3:24])[O:21][CH:20]([CH2:22][O:23][C:2]2[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3)[N:3]=2)[CH2:19][O:18]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7528SolketalHCID 24758Sodium hydrideHCID 23079398HCID 23079398, compound

Product 1

HCID 23079426HCID 23079426, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 2 g of N,N-dimethylformamide, 0.257 g of 5-chloro-3-(4-methylbenzyl)thio-1,2,4-thiadiazole and 0.145 g of 2,2-dimethyl-1,3-dioxolane-4-methanol were dissolved, and added 48 mg of sodium hydride (60% in oil) at about 0° C., followed by stirring at about 0° C. for 30 minutes 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 0.27 g of 5-(2,2-dimethyl-1,3-dioxolane-4-yl)methoxy-3-(4-methylbenzyl)thio-1,2,4-thiadiazole.

Workup

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

Sources & evidence

ORD record
ord-9e532c0ba40b4f99bff7ca3605cc762a
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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