Lawesson's reagent → HCID 86644319, compound

HRID 1770660Notes

Reaction equation

HRID 1770660 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][NH:14][CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=O)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][NH:14][CH2:15][C:16]([N:18]([CH3:20])[CH3:19])=[S:37])[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 68487077HCID 68487077, compound

Product 1

HCID 86644319HCID 86644319, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-[2-(3-butoxyphenyl)-(tert-butoxycarbonyl)ethylamino]-N,N-dimethylacetamide (0.38 g, 1.0 mmol) in dry toluene (20 ml), Lawesson's reagent (0.58 g, 1.2 mmol) was added one-pot and the mixture was heated to reflux and stirred for 2 h. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography (petroleum ether:AcOEt from 9:1 to 8:2) to give pure title compound as a colourless oil (0.11 g, 28% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by flash chromatography (petroleum ether:AcOEt from 9:1 to 8:2)

Sources & evidence

ORD record
ord-8af1ea34fbfc4d7480b290826cabfd31
Source dataset
uspto-grants-2016_02
Patent number
US09248116B2

Reaction notes

Loading…