Lawesson's reagent → 4-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamide

HRID 241518

Reaction equation

HRID 241518 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[Cl: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[Cl:16]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 668366994-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

Product 1

HCID 866857054-bromo-3-chloro-N-trimethylsilanylmethylthiobenzamideYield 123.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide (34.00 g, 106.0 mmol) in toluene (250 mL) was added Lawesson's reagent (30.45 g, 75.28 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 (31.3 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-883e5b94a177452c808aa72155b27f5a
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Linked notes

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