Reaction #46067

Reaction equation

Sodium hydride

Trifluoroacetamide

ammonium chloride

E-1,3-dichloropropene

→

N-(3-Chloro-allyl)-2,2,2-trifluoro-acetamide

Solvents

THF

water

Conditions

Workup

1. 1
   Otherthe temperature of the reaction with a water bath
2. 2
   workup.WAITAfter 2 min.
3. 3
   Temperaturethe reaction was heated
4. 4
   Temperatureto reflux for 45 min
5. 5
   TemperatureThe mixture is then cooled to room temperature
6. 6
   OtherThe mixture is transferred to a separatory funnel
7. 7
   Extractionextracted with ether (2×400 mL)
8. 8
   DryingThe combined organic layers were dried (MgSO4)
9. 9
   Concentrationconcentrated under reduced pressure
10. 10
    Otherto obtained a colorless oil that

Procedure

Trifluoroacetamide (10.44 g, 92.4 mmol) is dissolved in THF (30 mL). Sodium hydride (60% weight dispersion in mineral oil, 3.1 g, 77 mmol) is then added in small portions at room temperature while regulating the temperature of the reaction with a water bath. The mixture is stirred at room temperature for 5 min., after which E-1,3-dichloropropene (4.5 mL, 49.4 mmol) is added. After 2 min., the mixture thickened, and the reaction was heated to reflux for 45 min. The mixture is then cooled to room temperature, and saturated aqueous ammonium chloride (20 mL) and water (40 mL) are added. The mixture is transferred to a separatory funnel and extracted with ether (2×400 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to obtained a colorless oil that was used for the next step.

Source