Lawesson's reagent → 3,4-Dihydro-pyrano[3,4-c]pyridine-1-thione

HRID 1818909Notes

Reaction equation

HRID 1818909 reaction equation
[C:1]1(=O)[C:6]2=[CH:7][N:8]=[CH:9][CH:10]=[C:5]2[CH2:4][CH2:3][O:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1(C)C=CC=CC=1>[C:1]1(=[S:21])[C:6]2=[CH:7][N:8]=[CH:9][CH:10]=[C:5]2[CH2:4][CH2:3][O:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 442532Gentianadine

Product 1

HCID 251587463,4-Dihydro-pyrano[3,4-c]pyridine-1-thioneYield 120.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,4-dihydro-pyrano[3,4-c]pyridine-1-on (250 mg, 1.676 mmol) was dissolved in anhydrous toluene and stirred overnight at room temperature after adding Lawesson reagent (420 mg, 1.005 mmol). The mixture was evaporated under reduced pressure and a silica gel column chromatography (70% EtOAc/Hexane) was performed on the resulting residue and obtained 200 mg (72%) of 3,4-dihydro-pyrano[3,4-c]pyridine-1-thione in yellow solid.

Workup

  1. customThe mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5afca0544a8c455696df5025062929a1
Source dataset
uspto-grants-2009_10
Patent number
US07601736B2

Reaction notes

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