Dibutylamine → N,N-dibutylprop-2-enamide

HRID 1982514Notes

Reaction equation

HRID 1982514 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[C:10](Cl)(=[O:13])[CH:11]=[CH2:12]>C1(C)C=CC=CC=1>[CH2:1]([N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[C:10](=[O:13])[CH:11]=[CH2:12])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 13140Acryloyl chloride

Product 1

HCID 10419855N,N-dibutylprop-2-enamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
25 °C

Procedure

In a 2 liter 3-necked flask were combined 129 g (1 mol) di-(n-butyl)amine (Fisher Scientific) and 0.1 l dry toluene and cooled to 5° C. 46 g (0.5 mol) acryloyl chloride dissolved in 50 ml toluene were added slowly so the temperature remained below 10° C. After the addition the flask was warmed to 25° C. and the precipitate removed by filtration. 1 g DNPD was added, and after concentration on a rotary evaporator the product was distilled at 20 m torr and 61°-63° C. Yield 77 g (84%).

Workup

  1. customIn a 2 liter 3-necked flask were combined
  2. additionwere added slowly so the temperature
  3. customremained below 10° C
  4. additionAfter the addition the flask
  5. customthe precipitate removed by filtration
  6. addition1 g DNPD was added
  7. concentrationafter concentration
  8. customon a rotary evaporator the product
  9. distillationwas distilled at 20 m torr and 61°-63° C

Sources & evidence

ORD record
ord-d32b127a9f074f7fb5c15ce775969086
Source dataset
uspto-grants-1986_06
Patent number
US04596858

Reaction notes

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