2-Chloro-6-iodo-3-propyl-quinazolin-4-one → Proquinazid

Participants

Reaction Conditions

Reaction Steps

A portion of the sodium propoxide solution prepared above (87 g) was cooled to 1° C. and treated dropwise with the solution of 2-chloro-6-iodo-3-n-propyl-4(3H)-quinazolinone prepared in Step 2B above. The temperature was maintained at or below 0° C. and the addition took 2.5 h. After stirring at 0° C. for an additional 1.5 h, the reaction mixture was poured into 250 mL water. The phases were separated and the organic phase was washed two times each with 250 mL water. The organic phase was then evaporated under reduced pressure to give 53.4 g of a light yellow oil which solidified upon standing to a white solid. mp 60-62° C.; 1H NMR (CDCl3): δ8.49 (d,1H), 7.87 (dd,1H), 7.19 (d,1H), 4.43 (t,2H), 4.05 (m,2H), 1.85 (m,2H), 1.70 (m,2H), 1.05 (t,3H), 0.96 (t,3H).

Provenance & Evidence