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

HRID 241525Notes

Reaction equation

HRID 241525 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(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:26]2)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6](=[S:26])[NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[CH3:16]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 668364694-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide2×

Product 1

HCID 866910454-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzamideYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide (i.e. the product of Step 1, 32.8 g) in toluene (250 mL) was added 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (“Lawesson's reagent”, 31.3 g). The mixture was heated at reflux for 1 h, cooled to room temperature and concentrated. Purification by flash chromatography on silica gel afforded the title compound (30.3 g, 88%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7d40ad9089ba4048a7c25852758b6e10
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Reaction notes

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