Lawesson's reagent → HCID 14668765, compound

HRID 1947062Notes

Reaction equation

HRID 1947062 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=O)[C:4]=2[CH:3]=[CH:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[S:20])[C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 2802291,5,6,7-Tetrahydro-4H-indol-4-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 14668765HCID 14668765, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,5,6,7-tetrahydro-indol-4-one (4.51 g, 33.36 mmol) in dry THF (300 mL) was added Lawesson's reagent (3.495 g, 33.36 mmol) at 0° C. as a solid, in portions. The reaction mixture was warmed to RT and stirred for 35 min. The reaction mixture was then poured into saturated NaHCO3, the product extracted into Et2O, dried over MgSO4, filtered, evaporated, and dried under vacuum overnight. The product was purified by filtration through SiO2 using 30% EtOAc/hexane, evaporated to dryness, and dried under vacuum for 1 h to provide 1,5,6,7-tetrahydro-indole-4-thione (4.354 g, 86.3% yield).

Workup

  1. extractionthe product extracted into Et2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried under vacuum overnight
  6. filtrationThe product was purified by filtration through SiO2 using 30% EtOAc/hexane
  7. customevaporated to dryness
  8. customdried under vacuum for 1 h

Sources & evidence

ORD record
ord-415ba5673fb240058ed9761f23317f1e
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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