Propylamine → Proquinazid

Participants

Reaction Steps

To the remaining 320 mL solution of methyl 5-iodo-2-[(propoxythioxomethyl)amino]benzoate from Step C above was added 10.86 mL (0.132 mol) of propylamine. The reaction solution was heated at reflux overnight, concentrated to 1/3 volume under reduced pressure, and treated with 75 mL water added dropwise at room temperature. Following refrigeration at 0-5° C. overnight, an additional 25 mL H2O was added and cooling was continued for an additional 48 h. Filtration of the ensuing mixture provided 15.68 g of the title compound, 1H NMR (300 MHz, CDCl3): δ0.96 (t,3H); 1.06 (t,3H); 1.64-1.79 (m,2H); 1.81-1.92 (m,2H); 4.05 (t,2H); 4.43 (t,2H); 7.19 (d,1H); 7.85 (dd,1H); 8.49 (d,1H), m.p. 49-53° C.

Provenance & Evidence