Chloroacetyl chloride → 2-chloro-N-cyclohexyl-N-ethylacetamide

HRID 978020

Reaction equation

HRID 978020 reaction equation
[CH2:1]([NH:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH3:2].[Cl:10][CH2:11][C:12](Cl)=[O:13].C(N(CC)CC)C>C1C=CC=CC=1>[CH2:1]([N:3]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:12](=[O:13])[CH2:11][Cl:10])[CH3:2]

Participants

5

Procedure

N-Ethyl-cyclohexylamine (2.6 g) is dissolved in dry benzene (20 ml). To the solution are added dropwise with stirring chloroacetyl chloride (2.6 g) and triethylamine (2.4 g) under ice-cooling. The mixture is stirred under ice-cooling for one hour and further at room temperature for one hour. The reaction mixture is poured onto ice-water and extracted with ether. The ether layer is washed with an aqueous sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After distilling off the solvent, the resulting residue is distilled under reduced pressure to give N-ethyl-N-cyclohexyl-chloroacetamide (3 g), b.p. 118°-120° C./0.2 mmHg.

Workup

  1. temperaturecooling
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionextracted with ether
  4. washThe ether layer is washed with an aqueous sodium hydrogen carbonate solution
  5. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. distillationthe resulting residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-b0213538f2d74f159b65943b0958be63
Source dataset
uspto-grants-1987_05
Patent number
US04663323

Linked notes

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