N-(4-Phenoxyphenyl)acetamide → N-(4-Phenoxy-phenyl)-thioacetamide

HRID 538617Notes

Reaction equation

HRID 538617 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=O)[CH3:16])=[CH:10][CH:9]=1)[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:27])=CC=1>C1(C)C=CC=CC=1>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[S:27])[CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80579N-(4-Phenoxyphenyl)acetamideHCID 87949Lawesson's reagent

Product 1

HCID 59402779N-(4-Phenoxy-phenyl)-thioacetamideYield 86.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of N-(4-phenoxy-phenyl)-acetamide (1.20 g, 5.28 mmol) in 10 ml of toluene was added Lawesson's reagent (1.50 g, 3.70 mmol). The reaction mixture was heated at 120° C. for 2 h. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (5:95) as the eluent to provide the title compound (0.78 g, 60.7%).

Workup

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. customThe residue was purified by column chromatography on silica (60-120 M)

Sources & evidence

ORD record
ord-e571c8c8df594c3dbca6ee9ddc740d78
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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