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

HRID 488691ノート

反応式

HRID 488691 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b93701a9aa444ecab00fdb80d279d0ff
出典データセット
uspto-grants-2005_12
特許番号
USRE038921E1

反応ノート

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