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

HRID 973984Notes

Reaction equation

HRID 973984 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d954fdb73f324aaf82e534b97b658328
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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