Diethylamine → 4-chloro-N,N-diethylcrotonamide

HRID 1637718Notes

Reaction equation

HRID 1637718 reaction equation
[Cl:1][CH2:2]/[CH:3]=[CH:4]/[C:5](Cl)=[O:6].[CH2:8]([NH:10][CH2:11][CH3:12])[CH3:9]>CCOCC>[Cl:1][CH2:2]/[CH:3]=[CH:4]/[C:5]([N:10]([CH2:11][CH3:12])[CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 103969114-Chlorobut-2-enoyl chloride

Product 1

HCID 187999934-chloro-N,N-diethylcrotonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4-Chlorocrotonyl chloride (1.36 g, 9.80 mmol) in ether (20 ml) is combined with diethylamine in ether (5 ml) at -15° C. in a flame dried flask. The reaction is warmed to ambient temperature, stirred for 1 to 2 hours, quenched with water (30 ml), extracted with ethyl acetate (2×30 ml), washed with saline (30 ml), dried over sodium sulfate, and concentrated in vacuo to yield the crude 4-chloro-N,N-diethylcrotonamide.

Workup

  1. customdried flask
  2. customquenched with water (30 ml)
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washwashed with saline (30 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2fa9277bf12f466c87f632cff0cb0194
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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