Sodium Chloride → HCID 23032449, compound

HRID 917324Notes

Reaction equation

HRID 917324 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:15][C:2]2[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 23032449HCID 23032449, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2 ml of N,N-dimethylformamide were dissolved 150 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 154 mg of 4-chlorobenzyl alcohol, 43 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 0.5 hour under ice-cooling and for 4 hours at room temperature. The reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 170 mg of 5-(4-chlorobenzyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (4)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. extractionextracted with t-butyl methyl ether
  4. concentrationThe organic layer was concentrated
  5. customthe residue obtained

Sources & evidence

ORD record
ord-4924fd26a8054c43be4969fbec893fc2
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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