Tetrahydrofuran → HCID 18464819, compound

HRID 637188Notes

Reaction equation

HRID 637188 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=O)[CH3:15])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].O1CCCC1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C(OCC)(=O)C.ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[S:31])[CH3:15])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 87949Lawesson's reagentHCID 4153338N-[4-Methoxy-3-(methoxycarbonyl)phenyl]ethanimidic acid

Product 1

HCID 18464819HCID 18464819, compound

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Combine methyl 2-methoxy-5-acetamidobenzoate (2.23 g, 10 mmol) and tetrahydrofuran (1000 mL). Add Lawesson's reagent (2.02 g, 5 mmol). After 18 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 12% ethyl acetate/dichloromethane to give methyl 2-methoxy-5-thioacetamidobenzoate.

Workup

  1. customevaporate in vacuo
  2. customto give a residue

Sources & evidence

ORD record
ord-741eed41a5d04890a476b5129ed535d3
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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