Lawesson's reagent → HCID 45088408, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe mixture was heated for 2 hours
- temperatureunder reflux
- 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
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