Triethylamine → 4-(Acryloylamino)benzamide

HRID 968043Notes

Reaction equation

HRID 968043 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:21])[CH:19]=[CH2:20]>CN(C)C=O>[C:18]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1)(=[O:21])[CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 760794-Aminobenzamide

Product 1

HCID 869444-(Acryloylamino)benzamideYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Aminobenzamide (29 mmol) and triethylamine (33 mmol) were dissolved in dimethylformamide (100 mL) and acryloyl chloride (33 mmol) was dropped thereinto under ice-cooling. After the completion of the addition, the resultant mixture was stirred at room temperature for 2 hours. After filtering off the precipitate, the solvent was distilled off. Then the solid matter thus obtained was recrystallized from a solvent mixture of water with methanol to give 4-acrylamidobenzamide at a yield of 60%.

Workup

  1. temperatureunder ice-cooling
  2. additionAfter the completion of the addition
  3. filtrationAfter filtering off the precipitate
  4. distillationthe solvent was distilled off
  5. customThen the solid matter thus obtained
  6. customwas recrystallized from a solvent mixture of water with methanol

Sources & evidence

ORD record
ord-5d3d08bff6b14dea9901b4b8d55a0323
Source dataset
uspto-grants-2005_10
Patent number
US06956077B1

Reaction notes

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