N-Methylaniline → 3-chloro-N-methyl-N-phenylpropanamide

Participants

Reaction Steps

A solution of 107.2 g (1.00 mole) of N-methylaniline in 150 ml of tetrahydrofuran was added dropwise to a solution of 90.4 g (0.71 mole) of 3-chloropropionyl chloride in 250 ml of tetrahydrofuran. The reaction temperature was maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove a solid precipitate, and the filtrate was concentrated under reduced pressure to yield 130.0 g (91%) of a dark oil. An analytical sample was prepared by filtering the oil through a small bed of silica gel and eluting with ethyl acetate-hexane (1:5). The fractions containing the desired product were combined and concentrated under reduced pressure to give a light-yellow liquid. The liquid was partitioned between ethyl acetate and a saturated sodium bicarbonate solution. The ethyl acetate layer was washed with water and brine, dried (MgSO4), and concentrated under reduced pressure to give the title compound as a light-yellow oil.

Provenance & Evidence