Lawesson's reagent → HCID 10725969, compound

HRID 2395243Notes

Reaction equation

HRID 2395243 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][O:24][C:25]([CH:27]1[CH2:31][C:30](=O)[S:29][CH2:28]1)=[O:26]>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]([CH:27]1[CH2:31][C:30](=[S:10])[S:29][CH2:28]1)=[O:26]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10997333HCID 10997333, compound

Product 1

HCID 10725969HCID 10725969, compoundYield 144.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

207 g (0.51 mol) of Lawesson reagent are added at room temperature to a suspension of 149 g (0.93 mol) of tetrahydro-5-oxo-3-thiophenecarboxylic acid methyl ester in 1.23 litres of absolute toluene, and the mixture is boiled at reflux for 16 hours. Then the solvent is removed by distillation in vacuo, the residue is boiled at reflux for 20 minutes four times in one litre of a solvent mixture of petroleum ether and diethyl ether 1:1 each time, and the extract phase is in each case decanted off and concentrated. After distillation of the crude substance at 130°-140° C./0.03 mbar using a bulb tube, 129.5 g of orange oil are obtained.

Workup

  1. temperatureat reflux for 16 hours
  2. customThen the solvent is removed by distillation in vacuo
  3. temperatureat reflux for 20 minutes four times
  4. additionin one litre of a solvent mixture of petroleum ether and diethyl ether 1:1 each time
  5. customdecanted off
  6. concentrationconcentrated
  7. distillationAfter distillation of the crude substance at 130°-140° C./0.03 mbar

Sources & evidence

ORD record
ord-62d61c60a3cc497a87d204ddfec8e018
Source dataset
uspto-grants-1998_09
Patent number
US05814629

Reaction notes

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