Acetonitrile → 1-(2-Chlorophenyl)-3-(dimethylamino)prop-2-en-1-one
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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), N,N-dimethylformamide dimethyl acetal (707.0 g), and acetonitrile (dried over molecular sieves, 3.0 L) 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 (1L). 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) which was used without further purification.
Workup
- customTo a 5 liter, 3-necked flask equipped with a mechanical stirrer
- temperaturethermometer, reflux condenser
- customcapped with a nitrogen inlet
- customgiving an orange solution
- temperatureThe mixture was heated gradually
- temperaturemaintained
- temperatureat reflux for 18 hours
- temperatureAfter the dark red solution was cooled to room temperature
- customthe acetonitrile was evaporated
- customleaving a heavy red oil
- customThe toluene was evaporated
- customto afford the crude enamine which
- customwas further dried under high vacuum overnight
Sources & evidence
- ORD record
- ord-11ae2c96918744abaa958b77ac22fb94
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05486529
Reaction notes
Loading…