Dimethylamine, hydrochloride → 4-chloro-N,N-dimethylbutyramide

HRID 70394Notes

Reaction equation

HRID 70394 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].Cl.[CH3:9][NH:10][CH3:11].[OH-].[Na+]>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([N:10]([CH3:11])[CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 783704-Chlorobutyryl chloride

Product 1

HCID 898524-chloro-N,N-dimethylbutyramideYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-butyryl chloride (1.12 ml, 10.0 mmol) and dimethyl-amine hydrochloride (4.1 g, 50.0 mmol) in THF at 5° C. was added 2M NaOH (30 ml, 60.0 mmol) dropwise over 30 minutes while maintaining reaction temperature between 5-10° C. The reaction was stirred for additional 1.5 h and was concentrated, extracted with EtOAc (×2). The combined organic layer was washed with 1M HCl (×2), brine, dried over Na2SO4, and concentrated in vacuo to yield the title compound as colorless oil (1.5 g, ˜100%). The crude was used without further purification.

Workup

  1. temperaturewhile maintaining
  2. customreaction temperature between 5-10° C
  3. concentrationwas concentrated
  4. extractionextracted with EtOAc (×2)
  5. washThe combined organic layer was washed with 1M HCl (×2), brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5ef09a811a274f479750342b1dc697f9
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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