Chloroacetyl chloride → 2-chloro-N-methyl-N-octylacetamide

HRID 1914053Notes

Reaction equation

HRID 1914053 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>C(OCC)C>[CH3:6][N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3](=[O:4])[CH2:2][Cl:1]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 75538Octylmethylamine

Product 1

HCID 856901342-chloro-N-methyl-N-octylacetamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Chloroacetyl chloride in diethylether was added dropwise to N-methyloctylamine in diethylether at −2° C. The organic solution was returned to room temperature, followed by stirring for 3 hours. The resulting solution was successively washed with an aqueous 1 mol/L hydrochloric acid solution and water, and then dried over anhydrous sodium sulfate. After removal the solvent under vacuum, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=23:2) to give N-methyl-N-octyl-chloroacetamide (yield: 66.4%).

Workup

  1. customwas returned to room temperature
  2. washThe resulting solution was successively washed with an aqueous 1 mol/L hydrochloric acid solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal the solvent under vacuum
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=23:2)

Sources & evidence

ORD record
ord-7fa9884aa2974055beceb669fdc98013
Source dataset
uspto-grants-2013_12
Patent number
US08609898B2

Reaction notes

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