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

HRID 973984ノート

反応式

HRID 973984 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d954fdb73f324aaf82e534b97b658328
出典データセット
uspto-grants-1991_11
特許番号
US05066680

反応ノート

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