Lawesson's reagent → HCID 15230377, compound

HRID 1708396Notes

Reaction equation

HRID 1708396 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[C:18]1/[C:19](=O)[O:20][CH2:21][CH2:22]/1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1/[CH:17]=[C:18]1/[C:19](=[S:33])[O:20][CH2:21][CH2:22]/1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9950191HCID 9950191, compound

Product 1

HCID 15230377HCID 15230377, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (E)-3-[[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]methylene]-4,5-dihydro-2(3H)-furanone (386 mg, 1.11 mmol) and Lawesson's Reagent (273 mg, 0.68 mmol) in 15 mL of toluene is heated at reflux for 1.5 hours. The solution is concentrated in vacuo and purified by flash chromatography eluting with hexane:ethyl acetate (3:1) to provide 188 mg (47%) of (E)-3-[[2-[(2,6-dichloro-3-methylphenyl)amino]-phenyl]methylene]-4,5-dihydro-2(3H) - furanthione; mp = 163°-165° C. dec.

Workup

  1. temperatureat reflux for 1.5 hours
  2. concentrationThe solution is concentrated in vacuo
  3. custompurified by flash chromatography
  4. washeluting with hexane:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-bd0d55127bee420d8af404b0039ee164
Source dataset
uspto-grants-1994_10
Patent number
US05358964

Reaction notes

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