Acetic Anhydride → HCID 178474512, compound

Participants

Reaction Conditions

Reaction Steps

0.8 g (10.0 mmol) sodium acetate and 1.9 g (9.40 mmol) 7-nitro-3,4-dihydro-1H-naphthalen-2-one (prepared according to D. E. Nichols et al., J. Med. Chem. 1989, 32, 2128-2134) are dissolved in 40 ml acetic acid and cooled to 15° C. 0.5 g (3.19 mmol) bromine are added and the mixture is stirred for 0.1 hours, until the bromine has finished reacting completely. Then 0.8 g (10.5 mmol) thiourea are added. The reaction mixture is heated to 60° C. for 0.25 hours, then suction filtered and washed. The crystals are recrystallised from ethanol. Yield: 0.75 g (M.p.: 247-248° C.) 0.75 g (3.0 mmol) of the compound described previously are placed in 5 ml (49 mmol) acetic anhydride and refluxed for 0.1 hours. After cooling to ambient temperature the precipitate formed is suction filtered, washed with ethyl acetate and diethyl ether and dried. Yield: 0.8 g (M.p.: >315° C.)

Provenance & Evidence