Hydrochloric Acid → HCID 780872, compound

Participants

Reaction Conditions

Reaction Steps

Iminodiacetic acid (200 g, 1.50 mol) was dissolved in water (3 L) and sodium hydroxide (180 g, 4.5 mol) was added in small portions with stirring. After stirring for 15 minutes, p-toluenesulfonyl chloride (286.5 g, 1.5 mol) was added in small portions. The reaction mixture was heated to 80° C. for one hour, giving a clear solution. At the end of this time, the reaction solution was cooled in an ice bath to 10°--15° C., and concentrated HCl (110 ml) was added, precipitating the product as a white solid. This solid was filtered and washed with cold water, then dried in a vacuum oven at 55° C., giving 207.7 g (0.723 mol, 48.2% yield): mp 195°-196° C . (lit.* mp 191° C.); 1H NMR (DMSO-d6, 300 MHz) δ 2.38 (s, 3H), 3.66 (s, 4H), 7.39 (d, J=8.7 Hz, 2H), 7.65 (d, J=8.1 Hz); 13C NMR (DMSO-d6, 75 MHz) δ 20.90, 53.98, 126.55, 129.79, 136.70, 143.17, 171.77.

Provenance & Evidence