Chlorotrimethylsilane → HCID 58610416, compound

HRID 1594426Notes

Reaction equation

HRID 1594426 reaction equation
BrCCBr.C[Si](Cl)(C)C.[CH2:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14](I)[CH2:13]1)[CH3:11].Cl[C:20]1[S:24][N:23]=[C:22]([S:25][CH3:26])[N:21]=1>[Zn].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCCC1>[CH2:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([C:20]2[S:24][N:23]=[C:22]([S:25][CH3:26])[N:21]=2)[CH2:13]1)[CH3:11]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 64788929HCID 64788929, compound

Product 1

HCID 58610416HCID 58610416, compoundYield 47.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

439 mg of zinc powder and 63 mg of 1,2-dibromoethane was added into 7 ml of tetrahydrofurane under nitrogen atmosphere and the mixture was refluxed for 1 minute. After cooling to room temperature, 36 mg of trimethylsilyl chloride and 3.0 g of 3-ethylcyclohexyl iodide were added to the mixture, and the mixture was stirred for 6 hours at room temperature. Further, 561 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole and 137 mg of {1,1′-bis(diphenylphosphino)ferrocene} dichloro palladium(II) dichloromethane complex were added in the mixture, and the reaction mixture was refluxed for 17 hours. The reaction mixture was concentrated, and the residue subjected to silica gel column chromatography to give 384 mg of 5-(3-ethylcyclohexyl)-3-methylthio-1,2,4-thiadiazole.

Workup

  1. temperaturethe mixture was refluxed for 1 minute
  2. additionwere added in the mixture
  3. temperaturethe reaction mixture was refluxed for 17 hours
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-2834871382854769bc8f4b0e83b47ea7
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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