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 (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) 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-a42dc203f97a41bb97111496d24754f0
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05721222
Reaction notes
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