Benzyl Alcohol → 5-Benzyloxy-3-methylthio-1,2,4-thiadiazole

HRID 917322Notes

Reaction equation

HRID 917322 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[CH2:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH2:9]([O:16][C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 117085115-Benzyloxy-3-methylthio-1,2,4-thiadiazoleYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 11 ml of N,N-dimethylformamide were dissolved 190 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 123 mg of benzyl alcohol, 59 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 4.5 hours at room temperature. The reaction mixture was added to saturated ammonium 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 190 mg of 5-benzyloxy-3-methylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (1)).

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-89ed987568a54f469a164907b61f5677
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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