Pyridine → Ethyl 3-chloro-4-methylcarbanilate

Participants

Reaction Steps

Using a method analogous to that disclosed in Example 1, Step A, of U.S. Pat. No. 4,552,585, a solution of 10.0 grams (0.071 mole) of 3-chloro-4-methylaniline in 100 mL of chloroform was stirred, and 16.7 grams (0.212 mole) of pyridine was added. Ethyl chloroformate, 9.2 grams (0.085 mole), was then added dropwise during a 20 minute period. During the addition the reaction mixture temperature was held between 25°-30° C. with external cooling. Upon completion of addition the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was washed into a separatory funnel with 50 mL of chloroform, and the solution was washed with two 100 mL portions of water and 100 mL of aqueous 5% hydrochloric acid. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a waxy solid residue. The residue was recrystallized from hexane to yield 12.2 grams of ethyl (3-chloro-4-methylphenyl)carbamate; m.p. 51°-52° C.

Provenance & Evidence