Chloroacetic Acid → Chloro-N,N-diethylacetamide

HRID 1492489Notes

Reaction equation

HRID 1492489 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>[Cl:1][CH2:2][C:3]([N:9]([CH2:10][CH3:11])[CH2:7][CH3:8])=[O:5]

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 56.5%

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 HCl (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 1 hour at 0° C., the reaction was stirred at room temperature for 4 hours. The reaction mixture was then washed with water, 1N hydrochloric acid (until the aqueous phase was colorless) and saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title A compound as a yellow oil (9.3 g).

Workup

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

Sources & evidence

ORD record
ord-b9b586c8ed134e5eae1cb8aabbc7365b
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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