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

HRID 241511Notes

Reaction equation

HRID 241511 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 866910454-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamideYield 123.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-ab5fa87ae87945ecaa25b8f497c3b53f
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Reaction notes

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