Water → HCID 86735598, compound

Participants

Reaction Conditions

Reaction Steps

In 400 ml of benzene was suspended 4.15 g (10 mmol) of the sodium salt of 2'-hydroxy-5'-nitrohexadecananilide. The suspension was stirred and heated to boiling. Benzene, 100 ml was collected through a concentrator condenser. The condenser was then replaced with a reflux condenser on which a drying tube was mounted. The temperature of the mixture was lowered to 25° C and 4.84 g (20 mmol; 2.64 ml) of β-bromoethylphosphoryl dichloride was added. The slightly yellow solution was stirred for 1 hour at room temperature and then it was heated under reflux for 24 hours. After cooling to 10° C, 10 ml (0.56 mol) of water was added and the stirring was continued for 72 hours at room temperature. The precipitate 4.2 g was filtered from the mother liquor and washed with 100 ml of benzene. (Subsequent treatment of the mother liquor is described in part (d) of this example.) The dried and pulverized product was then suspended in 90 ml of 0.2 M sodium acetate buffer (pH 5.0) and stirred for 3 hours. The mixture was filtered through a coarse filter paper and the filtrate was acidified with 90 ml of 1 N hydrochloric acid and extracted twice with 180 ml of ethyl acetate. After evaporation of the solvent the residue (2.7 g) was recrystallized from 70 ml of acetone to yield 2.2 g (38%) of 2'-(β-bromoethylphosphoryl)-5'-nitrohexadecananilide. Mp 117°-118° C. The compound was water soluble as a sodium salt, 10-4M pH 3.7, and in 0.2 M sodium acetate buffer (pH 5.0), 100 mg per ml. It was insoluble in water; slightly soluble in ethyl ether; soluble in methyl and ethyl alcohol, ethyl acetate, acetone, methyl ethyl ketone, tetrahydrofuran, benzene and chloroform. Thin-layer chromatography: Chloroform-methanol-water (75:25:3). Rf 0.5. 2'-hydroxy-5'-nitrohexadecananilide, Rf 0.95). The ir spectrum displayed the following additional bands when compared with the spectrum of 2'-hydroxy-5'-nitrohexadecananilide, 1210 (P=0 str.), 1005, 950, 920 (P=0 (OH)), 730, 560 cm-1 (bromine ?).

Provenance & Evidence