Lawesson's reagent → 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamide

HRID 241511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241511
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=O)=[CH:4][C:3]=1[CH3:16].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[S:26])=[CH:4][C:3]=1[CH3:16]

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 668364694-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide

Produkt 1

HCID 866910454-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamideAusbeute 123,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 4-bromo-3-methyl-N-trimethylsilanylmethyl-benzamide (32.75 g, 109.1 mmol) in toluene (250 mL) was added Lawesson's reagent (31.32 g, 77.44 mmol) at room temperature. The mixture was heated at reflux for 1 h and cooled to ambient temperature. After adsorption of the reaction mixture on silica gel, the solvents were distilled off in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (30.3 g, 88%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. distillationAfter adsorption of the reaction mixture on silica gel, the solvents were distilled off in vacuum
  4. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ab5fa87ae87945ecaa25b8f497c3b53f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653000B2

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