Stannane, trimethylphenyl- → 3-Methylthio-5-phenyl-1,2,4-thiadiazole

HRID 900839

Reaction equation

HRID 900839 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.C[Sn](C)(C)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F-].[K+]>C1(C)C=CC=CC=1>[CH3:8][S:7][C:4]1[N:3]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[S:6][N:5]=1

Participants

5

Reactant 3

HCID 123095Stannane, trimethylphenyl-HCID 522689Potassium FluorideHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Product 1

HCID 230869103-Methylthio-5-phenyl-1,2,4-thiadiazoleYield 72.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 30 ml of toluene were added 500 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole, 794 mg of trimethylphenyltin and 346 mg of tetrakistriphenylphosphine palladium, and the mixture was heated under reflux for 8 hours in a nitrogen atmosphere. Then, the reaction mixture was cooled to room temperature, and a 20% aqueous potassium fluoride solution was added to the reaction mixture, followed by stirring. This mixture was filtered through Celite, and the filtrate was concentrated. The resulting residue was subjected to silica gel column chromatography to obtain 455 mg of 3-methylthio-5-phenyl-1,2,4-thiadiazole.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours in a nitrogen atmosphere
  3. filtrationThis mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-32428475ae3e40a3b5eaaa00620bcfc6
Source dataset
uspto-grants-2008_04
Patent number
US07361675B2

Linked notes

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