2-Chlorobenzoyl isocyanate → 3-(4-[4-Chloro-5,6,7,8-tetrahydro-1-naphthoxy]-3,5-dimethylphenyl)-1-(2-chlorobenzoyl) urea

Participants

Reaction Conditions

Reaction Steps

To a solution containing 3.0 g of 4-(4-chloro-5,6,7,8-tetrahydro-1-naphthoxy)-3,5-dimethylaniline in 40 mL of toluene under an atmosphere of nitrogen and heated to 70° C. (internal) was slowly added a solution containing 2.7 g of 2-chlorobenzoyl isocyanate in 5 mL of toluene. The resulting mixture was heated at 70° C. for 1/2 hour. The reaction mixture was cooled to 0° C. and filtered. The collected solid was washed with toluene and then hexane. It was dried under vacuum to afford 3.58 g of a white solid, mp. 224°-226° C. NMR (DMSO-d6): 1.7-2.2 (m, 10H, contains singlet at 2.03), 2.7-3.0 (m, 4H), 6.07 (d, J=9 Hz, 1H), 7.07 (d, J=9 Hz, 1H), 7.07 (d, J=9 Hz, 1H), 7.4-7.7 (m, 4H), 10.38 (S, 1H), 11.20 (S, 1H).

Provenance & Evidence