Thionyl Chloride → N-(4-chloro-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

HRID 973984Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 973984
S(Cl)([Cl:3])=O.O[CH2:6][C:7]#[C:8][CH2:9][NH:10][C:11](=[O:26])[C:12]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O.C(Cl)(Cl)Cl>[Cl:3][CH2:6][C:7]#[C:8][CH2:9][NH:10][C:11](=[O:26])[C:12]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 2

HCID 24386Thionyl ChlorideHCID 15023453N-(4-hydroxy-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

Produkt 1

HCID 15023451N-(4-chloro-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Thionyl chloride (4.8 ml) was added dropwise to a mixture of N-(4-hydroxy-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (6.56 g) and N,N-dimethylformamide (5 drops) in dry chloroform (145 ml) at 0° C. and the reaction mixture was refluxed for 1 hour. The mixture was washed successively with water, 1N aqueous sodium hydroxide solution, and sodium chloride, aqueous solution, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent to give N-(4-chloro-2-butynyl)-2-cyclohexyl-2-hydroxy-2-phenylacetamide as white powder (6.7 g).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. washThe mixture was washed successively with water, 1N aqueous sodium hydroxide solution, and sodium chloride, aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-d954fdb73f324aaf82e534b97b658328
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05066680

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