Lawesson's reagent → 5-Bromo-2-chloro-1-(2-phenyl-5-thiazolylmethyl)benzene

HRID 1625890Notes

Reaction equation

HRID 1625890 reaction equation
[C:1]([NH:9][CH2:10][C:11](=O)[CH2:12][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=1[Cl:20])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C=CC=CC=1>[Br:19][C:17]1[CH:16]=[CH:15][C:14]([Cl:20])=[C:13]([CH2:12][C:11]2[S:31][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:9][CH:10]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 666074521-(3-Benzoylamino-2-oxopropyl)-5-bromo-2-chlorobenzene

Product 1

HCID 666086455-Bromo-2-chloro-1-(2-phenyl-5-thiazolylmethyl)benzeneYield 72.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the above 1-(3-benzoylamino-2-oxopropyl)-5-bromo-2-chlorobenzene (710 mg) in toluene (20 ml) was added Lawesson reagent (2.35 g), and the mixture was heated under reflux for 2 hours. The reaction mixture was cooled, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10) to give the desired 5-bromo-2-chloro-1-(2-phenyl-5-thiazolylmethyl)benzene (512 mg) as a colorless solid. APCI-Mass m/Z 364/366 (M+H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10)

Sources & evidence

ORD record
ord-680c580525ab40d3a166e226c155ed71
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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