Sodium Chloride → 5-(6-Chloro-2-pyridylmethyloxy)-3-methylthio-1,2,4-thiadiazole

HRID 917336Notes

Reaction equation

HRID 917336 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[Cl:9][C:10]1[N:15]=[C:14]([CH2:16][OH:17])[CH:13]=[CH:12][CH:11]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[Cl:9][C:10]1[N:15]=[C:14]([CH2:16][O:17][C:2]2[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 182139(6-Chloropyridin-2-yl)methanolHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 121513905-(6-Chloro-2-pyridylmethyloxy)-3-methylthio-1,2,4-thiadiazoleYield 12.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 3 g of N,N-dimethylformamide were dissolved 251 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 188 mg of 6-chloro-2-pyridylmethyl alcohol, 72 mg of sodium hydride (60% in oil) was added thereto at room temperature, and the reaction mixture was stirred for 30 minutes. 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 44 mg of 5-(6-chloro-2-pyridylmethyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (35)).

Workup

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

Sources & evidence

ORD record
ord-82714a44eb96410eb352b0cbd4eb50ef
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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