Aniline → 3-Methyl-N-phenylbut-2-enamide

HRID 1382916Notes

Reaction equation

HRID 1382916 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]([CH3:14])=[CH:10][C:11](Cl)=[O:12]>C(Cl)(Cl)Cl>[CH3:8][C:9]([CH3:14])=[CH:10][C:11]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 6115AnilineHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 123870223-Methyl-N-phenylbut-2-enamideYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 4.1 g (0.44 mol) of aniline in 200 ml of chloroform, at 25° C., was added slowly a solution of 25 g (0.21 mol) of 3-methylcrotonoyl chloride in 100 ml of chloroform. The reaction mixture was refluxed for 1.5 hours, and then the precipitate was removed by filtration. The chloroform solution was washed successively with 1N hydrochloric acid and saturated sodium bicarbonate solution, and then it was dried (MgSO4) and evaporated in vacuo. This gave 33.5 g (91% yield) of the title compound as a solid, mp 122°-125° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 1.5 hours
  2. customthe precipitate was removed by filtration
  3. washThe chloroform solution was washed successively with 1N hydrochloric acid and saturated sodium bicarbonate solution
  4. dry with materialit was dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0f4e303ad2a244a0bfb9ea1a5510b630
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

Loading…