Aniline → N-Phenylacrylamide

HRID 1596449

Reaction equation

HRID 1596449 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]1([NH2:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[C:6]1([NH:12][C:1](=[O:4])[CH:2]=[CH2:3])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 13140Acryloyl chloride

Product 1

HCID 221792N-PhenylacrylamideYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acryloyl chloride (28.5 mL; 350 mmol) was added to a stirred solution of phenylamine (30 mL; 320 mmol) and TEA (56 mL; 400 mmol) in THF (1 L) at 0° C. The reaction mixture was stirred for 3 h, poured onto brine and extracted with diethyl ether. The organic layer was dried, concentrated and recrystallized from hexane:EtOAc (3:1) to give the sub-title compound in a 79% yield.

Workup

  1. additionpoured onto brine
  2. extractionextracted with diethyl ether
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customrecrystallized from hexane:EtOAc (3:1)

Sources & evidence

ORD record
ord-9dd75fc3027048f985b3ab018e1338b8
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Linked notes

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