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

HRID 704118Notes

Reaction equation

HRID 704118 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-57ed0e5675ce40e8a7585086ff3334a7
Source dataset
uspto-grants-1991_01
Patent number
US04985585

Reaction notes

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