Lawesson's reagent → HCID 45088408, compound

HRID 497079Notes

Reaction equation

HRID 497079 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH3:23][N:24]1[C:28](=O)[CH2:27][CH2:26][C@@H:25]1[CH2:30][C:31]#[N:32]>C1C=CC=CC=1>[CH3:23][N:24]1[C:28](=[S:10])[CH2:27][CH2:26][C@@H:25]1[CH2:30][C:31]#[N:32]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 45087748HCID 45087748, compound

Product 1

HCID 45088408HCID 45088408, compoundYield 157.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Lawesson's reagent (Tokyo Kasei Kogyo) (2.26 g, 5.6 mmols) was added to a benzene (40 ml) solution of the 2-((2R)-1-methyl-5-oxopyrrolidin-2-yl)ethanenitrile (1.48 g, 10.7 mmols), and the mixture was heated for 2 hours under reflux. The solvent was distilled off under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 80 g, MeOH—CHCl3 5:95 v/v) to obtain 2-((2R)-1-methyl-5-thioxopyrrolidin-2-yl)ethanenitrile (1.36 g, 82.8%).

Workup

  1. temperaturethe mixture was heated for 2 hours
  2. temperatureunder reflux
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5d05cd1799404b2784de02a3862c47b0
Source dataset
uspto-grants-2005_09
Patent number
US06949553B2

Reaction notes

Loading…