Potassium Carbonate → Ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio)-2-propylphenoxy)butyrate

HRID 488691Notes

Reaction equation

HRID 488691 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]([S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([OH:15])[C:7]=1[CH2:16][CH2:17][CH3:18])=[O:4].Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[C:12]([C:9]1[C:8]([O:15][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:7]([CH2:16][CH2:17][CH3:18])[C:6]([S:5][C:3](=[O:4])[N:2]([CH3:1])[CH3:19])=[CH:11][CH:10]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 76300Ethyl 4-bromobutyrateHCID 2801555S-(4-Acetyl-3-hydroxy-2-propylphenyl) dimethylcarbamothioate

Product 1

HCID 15712394Ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio)-2-propylphenoxy)butyrateYield 84.2%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of (4-(N,N-dimethylcarbamoylthio)-2-hydroxy-3-propylphenyl)ethanone (26.6 g), ethyl 4-bromobutyrate (92.9 g), potassium iodide (1 g) and potassium carbonate (26.1 g) in acetone (200 ml) was heated and refluxed with stirring. Each of potassium carbonate (13 g) was added thereto after 9 hours and 14 hours, and the mixture was heated and refluxed with stirring for total 29 hours. Then, inorganic materials were separated and the solution was concentrated under a reduced pressure. The resultant residue was purified through silica-gel column chromatography (eluting with hexane, then benzene and finally benzene:ethyl acetate=9:1) to give ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio) -2-propylphenoxy)butyrate (31.5 g, 84.2%) as light brown crystal, mp 60-63° C.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed
  3. temperature14 hours, and the mixture was heated
  4. temperaturerefluxed
  5. stirringwith stirring for total 29 hours
  6. customThen, inorganic materials were separated
  7. concentrationthe solution was concentrated under a reduced pressure
  8. customThe resultant residue was purified through silica-gel column chromatography (
  9. washeluting with hexane

Sources & evidence

ORD record
ord-b93701a9aa444ecab00fdb80d279d0ff
Source dataset
uspto-grants-2005_12
Patent number
USRE038921E1

Reaction notes

Loading…