Lawesson's reagent → HCID 45088409, compound

HRID 497073Notes

Reaction equation

HRID 497073 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 45087749HCID 45087749, compound

Product 1

HCID 45088409HCID 45088409, compoundYield 160.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Lawesson's reagent (Tokyo Kasei Kogyo) (1.54 g, 3.8 mmols) was added to a benzene (25 ml) solution of the 2-((2S)-1-methyl-5-oxopyrrolidin-2-yl)ethanenitrile (1.05 g, 7.6 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 60 g, MeOH—CHCl3 1:9 v/v) to obtain 2-((2S)-1-methyl-5-thioxopyrrolidin-2-yl)ethanenitrile (941 mg, 80.6%): IR νmax (film) cm−1: 2246. 1H-NMR (CDCl3)δ: 4.20-4.10 (1H, m), 3.30 (3H, s), 3.25-2.98 (2H, m), 277 (1H, dd, J=17.0, 4.9 Hz), 2.68 (1H, dd, J=17.0, 6.6 Hz), 2.50-2.36 (1H, m), 2.06-1.94 (1H, m). MS m/z: 154 (M+), 114 (100%). HRMS: Calcd. for C7H10N2S: 154.0565 (M+). Found: 154.0561 (M+).

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-df7ac4d18b9e413b86b02e30d1859a7a
Source dataset
uspto-grants-2005_09
Patent number
US06949553B2

Reaction notes

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