Chlorotrimethylsilane → 5-(2-Methylcyclohexyl)-3-methylthio-1,2,4-thiadiazole

HRID 1594423

Reaktionsgleichung

Reaktionsgleichung von HRID 1594423
BrCCBr.C[Si](Cl)(C)C.[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1I.Cl[C:19]1[S:23][N:22]=[C:21]([S:24][CH3:25])[N:20]=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>[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:19]1[S:23][N:22]=[C:21]([S:24][CH3:25])[N:20]=1

Komponenten

8

Edukt 4

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 5275691-Iodo-2-methylcyclohexaneHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazole

Produkt 1

HCID 586104425-(2-Methylcyclohexyl)-3-methylthio-1,2,4-thiadiazoleAusbeute 27,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

583 mg of zinc powder and 83 mg of 1,2-dibromoethane was added into 9 ml of tetrahydrofurane under nitrogen atmosphere and the mixture was refluxed for 1 minute. After cooling to room temperature, 49 mg of trimethylsilyl chloride and 3.0 g of 2-methylcyclohexyl iodide were added to the mixture, and the mixture was stirred for 6 hours at room temperature. Further, 1.49 g of 5-chloro-3-methylthio-1,2,4-thiadiazole and 109 mg of {1,1′-bis(diphenylphosphino)ferrocene} dichloro palladium(II) dichloromethane complex were added in the mixture, and the reaction mixture was stirred for 15 hours at room temperature and refluxed for 5 hours. The reaction mixture was concentrated, and the residue subjected to silica gel column chromatography to give 564 mg of 5-(2-methylcyclohexyl)-3-methylthio-1,2,4-thiadiazole.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 1 minute
  2. additionwere added in the mixture
  3. stirringthe reaction mixture was stirred for 15 hours at room temperature
  4. temperaturerefluxed for 5 hours
  5. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9269355bdc1e4bf4acd454efa40eb400
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07301032B2

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