Sodium Chloride → 5-(2-Chlorobenzyloxy)-3-methylthio-1,2,4-thiadiazole

HRID 917323Notes

Reaction equation

HRID 917323 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].Cl[C:13]1[S:17][N:16]=[C:15]([S:18][CH3:19])[N:14]=1.[Cl-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][C:13]1[S:17][N:16]=[C:15]([S:18][CH3:19])[N:14]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 288102-Chlorobenzyl alcoholHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 121513785-(2-Chlorobenzyloxy)-3-methylthio-1,2,4-thiadiazoleYield 45.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into 2 ml of N,N-dimethylformamide was dissolved 215 mg of 2-chlorobenzyl alcohol, 59 mg of sodium hydride (60% in oil) was added thereto under ice-cooling. After stirring for 30 minutes, a solution of 250 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole in 2 ml of N,N-dimethylformamide was added dropwise into the mixture and the reaction mixture was stirred for 0.5 hour under ice-cooling and for 2 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 188 mg of 5-(2-chlorobenzyloxy)-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (2)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringthe reaction mixture was stirred for 0.5 hour under ice-
  4. extractionextracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated
  6. customthe residue obtained

Sources & evidence

ORD record
ord-58b1777af5b24f2aaa29a22ac9e1e0f5
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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