Lawesson's reagent → HCID 60088435, compound

HRID 2053717Notes

Reaction equation

HRID 2053717 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[F:23][C:24]1[CH:34]=[CH:33][C:27]([CH2:28][NH:29][C:30](=O)[CH3:31])=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:34]=[CH:33][C:27]([CH2:28][NH:29][C:30](=[S:10])[CH3:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 3532104N-(4-Fluorobenzyl)acetamide

Product 1

HCID 60088435HCID 60088435, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Step c) Add Lawesson reagent (1.8 g, 3.6 mmol) to N-(4-fluorobenzyl)acetamide (0.9 g, 5.4 mmol) in 50 mL of toluene and heat to 80° C. for 12 hours. Remove solvent under reduced pressure. Purify the residue by column chromatography (silica gel, Acetone: Hexane=20:80) to give a mixture. Wash with ether and discard insoluble solid impurities by filtration. Remove solvent under reduced pressure to give N-(4-fluorobenzyl)-thioacetamide (0.7 gm) in 71% as a yellow solid: MS 184 (MH+).

Workup

  1. customPurify the residue by column chromatography (silica gel, Acetone: Hexane=20:80)
  2. customto give a mixture
  3. washWash with ether and discard insoluble solid impurities by filtration

Sources & evidence

ORD record
ord-42c8a591a043485ab04ae41ae2521257
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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