Lawesson's reagent → Oxane-4-carbothioamide

HRID 1497648Notes

Reaction equation

HRID 1497648 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=O)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:19])=CC=1.C([O-])(O)=O.[Na+]>C1COCC1>[O:1]1[CH2:6][CH2:5][CH:4]([C:7](=[S:19])[NH2:9])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 13197203Oxane-4-carboxamide

Product 1

HCID 13197204Oxane-4-carbothioamideYield 106.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydro-2H-pyran-4-carboxamide (2 g, 15.5 mmol) was suspended in dry THF (20 mL) and Lawesson's reagent (3.13 g, 7.75 mmol) was added. After refluxing for 4 h the mixture was poured into a saturated NaHCO3 aqueous solution (200 mL) and then extracted with diethylether (4×100 mL). The organic layer was dried over Na2SO4 and evaporated to dryness, affording 1.2 g (54%) of the title compound.

Workup

  1. temperatureAfter refluxing for 4 h the mixture
  2. extractionextracted with diethylether (4×100 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-1d67f28c400b4744861661b0784d1160
Source dataset
uspto-grants-2015_12
Patent number
US09199979B2

Reaction notes

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