In a
5-l. three-necked flask mounted on a
steam bath in the
hood and equipped with a
mechanical stirrer (Note
1) and a
wide-bore condenser (Note
1) is placed
1.4 kg. (1.1 l.) of carbon disulfide. Through the open neck of the flask
202 g. (1.5 moles) of acetanilide and
300 g. (2.66 moles) of chloroacetyl chloride (Note
2) are introduced. The mixture is vigorously stirred while
600 g. (4.5 moles) of aluminum chloride is added in 25–50 g. portions over a period of 20–30 minutes; the neck of the flask is stoppered between additions (Note
3). After the addition of the last portion of
aluminum chloride, the mixture is heated at reflux temperature for 30 minutes while stirring is continued. Heating and stirring are discontinued and the mixture is allowed to stand for 3 hours, during which time it separates into layers. The upper layer (
carbon disulfide) is decanted, and the viscous red-brown lower layer is poured cautiously with stirring into about 1 kg. of finely crushed ice to which
100 ml. of concentrated hydrochloric acid has been added. After the hydrolysis of the
aluminum chloride, the product crystallizes as a white solid, which is collected on a
Büchner funnel and washed well with water. It is then transferred to a
beaker where it is thoroughly washed by stirring with sufficient
95% ethanol to give a fluid slurry. The solid is again collected on the funnel. After drying in the air it melts at
213–214° and weighs
250–265 g. (
79–83%). It can be recrystallized from
95% ethanol (about 1 l. of the solvent being required for
40 g. of the solid) as fine white crystals melting at
216°; the recovery in the recrystallization, without reworking of the mother liquor, is about
70%.