Lawesson's reagent → 3-Iodothiobenzamide

HRID 2216880Notes

Reaction equation

HRID 2216880 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[S:20]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 2024253-Iodobenzamide

Product 1

HCID 27593753-IodothiobenzamideYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-iodobenzamide (500 mg, 2.0 mmol) in toluene (5 mL) was treated with Lawesson's reagent (404 mg, 1 mmol) and the mixture heated at reflux for 1.6 hours. After cooling, silica gel chromatography afforded 260 mg (99% yield) of 3-iodothiobenzamide, as a yellow solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.6 hours
  3. temperatureAfter cooling

Sources & evidence

ORD record
ord-ac53daa4d41f42e0ae4df53964d8081d
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

Loading…