Lawesson's reagent → dihydro-2,2,5,5-tetramethyl-4-ethylaminomethylene-3(2H)furanthione

HRID 1195630Notes

Reaction equation

HRID 1195630 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6](=O)[C:5](=[CH:8][NH:9][CH2:10][CH3:11])[C:4]([CH3:13])([CH3:12])[O:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>COCCOC>[CH3:1][C:2]1([CH3:14])[C:6](=[S:24])[C:5](=[CH:8][NH:9][CH2:10][CH3:11])[C:4]([CH3:13])([CH3:12])[O:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 53707148dihydro-2,2,5,5-tetramethyl-4-ethylaminomethylene-3(2H)furanone

Product 1

HCID 53796694dihydro-2,2,5,5-tetramethyl-4-ethylaminomethylene-3(2H)furanthione

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of dihydro-2,2,5,5-tetramethyl-4-ethylaminomethylene-3(2H)furanone (1.0 g, 5.1 mmol) and Lawesson's Reagent (1.1 g, 2.7 mmol) was stirred in 20 mL of DME for 20 min. at room temperature. The solvent was evaporated and the residue was dissolved in methylene chloride and eluted through a plug of silica gel/basic alumina 1/1 (CH2Cl2). The eluant was evaporated to leave dihydro-2,2,5,5-tetramethyl-4-ethylaminomethylene-3(2H)furanthione as an orange solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washeluted through a plug of silica gel/basic alumina 1/1 (CH2Cl2)
  4. customThe eluant was evaporated

Sources & evidence

ORD record
ord-996cc9fd0361419790e07f1c64f28d53
Source dataset
uspto-grants-1992_05
Patent number
US05112595

Reaction notes

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