Acetonitrile → 1-(2-Chlorophenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 441185Notes

Reaction equation

HRID 441185 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15].C(#N)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH:9]=[CH:13][N:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 538407941-(2-Chlorophenyl)-3-(dimethylamino)prop-2-en-1-oneYield 101.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
83 °C

Procedure

To a 5 liter, 3-necked flask equipped with a mechanical stirrer, thermometer, reflux condenser capped with a nitrogen inlet, and a heating mantle were added o-chloroacetophenone (305.8 g, 1.98 mol), N,N-dimethylformamide dimethyl acetal (707.0 g, 5.93 mol), and acetonitrile (dried over molecular sieves, 3.0 L) at room temperature, giving an orange solution. The mixture was heated gradually to reflux (83° C.) over 1.5 hours, then maintained at reflux for 18 hours. After the dark red solution was cooled to room temperature, the acetonitrile was evaporated, leaving a heavy red oil. The oil was redissolved in toluene (1 L). The toluene was evaporated to afford the crude enamine which was further dried under high vacuum overnight to afford 2'-chloro-3-dimethylaminopropenophenone (422 g, quantitative) which was used without further purification.

Workup

  1. customTo a 5 liter, 3-necked flask equipped with a mechanical stirrer
  2. temperaturethermometer, reflux condenser
  3. customcapped with a nitrogen inlet
  4. customgiving an orange solution
  5. temperatureThe mixture was heated gradually
  6. temperaturemaintained
  7. temperatureat reflux for 18 hours
  8. temperatureAfter the dark red solution was cooled to room temperature
  9. customthe acetonitrile was evaporated
  10. customleaving a heavy red oil
  11. customThe toluene was evaporated
  12. customto afford the crude enamine which
  13. customwas further dried under high vacuum overnight

Sources & evidence

ORD record
ord-66680af7fb474ba797d25cf8597c8002
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

Loading…