Lawesson's reagent → 3,3,3-Trifluoro-2,2-dimethyl-thiopropionamide

HRID 1807703Notes

Reaction equation

HRID 1807703 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([NH2:6])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1>C1COCC1>[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([NH2:6])=[S:20]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 575162793,3,3-Trifluoro-2,2-dimethyl-propionamide

Product 1

HCID 580927173,3,3-Trifluoro-2,2-dimethyl-thiopropionamideYield 129.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.05 g (6.77 mmol) 3,3,3-trifluoro-2,2-dimethyl-propionamide and 1.48 g (3.66 mmol) Lawesson's reagent in 32 ml dry THF was stirred at reflux temperature for 20 h. After that the reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography on silicagel (heptane, EtOAc) to afford 0.81 g of the title compound as pure white crystals. MS: M+H=172.

Workup

  1. temperatureat reflux temperature for 20 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silicagel (heptane, EtOAc)

Sources & evidence

ORD record
ord-df2a498bbddb41b89b5c66f21c6077a4
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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