Chloroacetic Acid → Chloro-N,N-diethylacetamide

HRID 1953843Notes

Reaction equation

HRID 1953843 reaction equation
[Cl:1][CH2:2][C:3]([OH:5])=O.Cl.[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>C(Cl)Cl>[CH2:7]([N:9]([CH2:10][CH3:11])[C:3](=[O:5])[CH2:2][Cl:1])[CH3:8]

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10197650Diethylammonium chloride

Product 1

HCID 16844Chloro-N,N-diethylacetamideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of chloroacetic acid (10 g, 0.11 mol) in methylene chloride (530 mL) at 0° C. was added diethylamine hydrochloric acid (15.3 g, 0.14 mol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (26.4 g, 0.14 mol) and 4-methyl morpholine (29 mL, 0.27 mol). After the reaction stirred one hour at 0° C., the reaction was stirred at room temperature for four hours. The reaction mixture was then washed with water, 1N hydrochloric acid (until the aqueous phase was colorless), and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow oil (9.3 g, 58%) which was used directly in the next step.

Workup

  1. stirringthe reaction was stirred at room temperature for four hours
  2. washThe reaction mixture was then washed with water, 1N hydrochloric acid (until the aqueous phase
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76fff99c834c40bb8e3ab04082719b00
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

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