Lawesson's reagent → tert-Butyl N-[4-(3-amino-3-thioxopropyl)-2-pyridyl]carbamate

HRID 1828413Notes

Reaction equation

HRID 1828413 reaction equation
[NH2:1][C:2](=O)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>O1CCCC1>[NH2:1][C:2](=[S:29])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22063511tert-Butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]carbamate

Product 1

HCID 22063705tert-Butyl N-[4-(3-amino-3-thioxopropyl)-2-pyridyl]carbamateYield 152.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Under argon atmosphere, tert-butyl N-[4-(3-amino-3-oxopropyl)-2-pyridyl]-carbamate (11.79 g, 44.44 mmol) dissolved in tetrahydrofuran (100 ml) was added with Lawesson's reagent (9 g, 22.22 mmol) and stirred at 70-80° C. for 30 minutes. After the reaction mixture was returned to room temperature, the solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform chloroform:methanol=20:1) to obtain 9.544 g (76%) of the title compound as pale yellow crystals.

Workup

  1. customwas returned to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-0a8f66eeb484472895f9ff399e033914
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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