Acetyl chloride → N-Phenylbutanamide
Reaction equation
C([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])C.[CH2:10](N(CC)CC)[CH3:11].[C:17](Cl)(=[O:19])[CH3:18]>>[CH2:10]([CH2:18][C:17]([NH:5][C:4]1[CH:3]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:19])[CH3:11]Participants
Conditions
- Temperature
- 2.5 °C
Procedure
2-Ethylaniline (82.6 mmol, 10 gams) was taken in round bottom flask equipped with a liquid addition funnel and a guard tube. Triethylamine (165 mmol, 16.69 grams) was added to it in one lot. The mass, thus obtained, was cooled to 0-5° C. and added acetyl chloride (123 mmol, 9.73 grams) drop wise, while maintaining the mass temperature below 10° C. After addition of acetyl chloride, cooling was removed and reaction was stirred at 25-28° C. for a period of 3 hours. After completion of the reaction, the reaction mixture was poured onto 200 mL of ice water and aqueous layer was extracted with dichloromethane (2×100 mL). The combined dichloromethane extracts were then washed with water, brine and dried over anhydrous magnesium sulfate. The volatiles were removed under the reduced pressure to obtain 14.09 grams of compound.
Workup
- customequipped with a liquid addition funnel and a guard tube
- customThe mass, thus obtained
- temperaturewhile maintaining the mass temperature below 10° C
- temperaturecooling
- customwas removed
- customreaction
- customAfter completion of the reaction
- extractionwas extracted with dichloromethane (2×100 mL)
- washThe combined dichloromethane extracts were then washed with water, brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe volatiles were removed under the reduced pressure
Sources & evidence
- ORD record
- ord-843fd02b7bad4100b3b0954ecec0fb69
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003670B2
Reaction notes
Loading…