Chlorotrimethylsilane → HCID 58610426, compound

HRID 1594420Notes

Reaction equation

HRID 1594420 reaction equation
BrCCBr.C[Si](Cl)(C)C.[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13](I)[CH2:12]1.Cl[C:19]1[S:23][N:22]=[C:21]([S:24][CH3:25])[N:20]=1>[Zn].O1CCCC1>[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:19]2[S:23][N:22]=[C:21]([S:24][CH3:25])[N:20]=2)[CH2:12]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 15433602HCID 15433602, compound

Product 1

HCID 58610426HCID 58610426, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
65 °C

Procedure

1.31 g of zinc foil (99.998%) and 190 mg of 1,2-dibromoethane was added into 2 ml of tetrahydrofurane under nitrogen atmosphere and the mixture was heated in an oil bath at 65° C. for 1 minute. After cooling to room temperature, 0.1 ml of trimethylsilyl chloride, 2.14 g of 3-methylcyclohexyl iodide and 10 ml of tetrahydrofuran were added to the mixture, and the mixture was exposed to ultrasonic wave in a water bath for 4 hours. Further, 1.31 g of 5-chloro-3-methylthio-1,2,4-thiadiazole, 390 mg of {1,1′-bis(diphenylphosphino)ferrocene} dichloro palladium(II) dichloromethane complex and 10 ml of tetrahydrofuran were added in the mixture, and the reaction mixture was stirred for 3.5 days at room temperature. The reaction mixture was concentrated, and the residue subjected to silica gel column chromatography to give 790 mg of 5-(3-methylcyclohexyl)-3-methylthio-1,2,4-thiadiazole.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ae2304159dd14e8a8d2be00a29786bf4
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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