Urea → 4-chloro-1-iodo-2-nitrobenzene

Participants

Reaction Steps

A 1M aqueous solution of sodium nitrite (50 milliliters (mL)) was added dropwise to a cold (3° C.) stirred mixture of 4-chloro-2-nitroaniline (8.63 grams (g), 50 millimoles (mmol)) in 6M HCl (150 mL) over a 45 minute (min) period with subsequent addition of about 5 g of urea during 30 min. An aqueous solution of potassium iodide (60 mL, 1M) was dripped into the resulting orange solution over a period of 35 min at 5° C. After an additional 45 min, the desired product, which had separated from solution, was isolated by filtration and then dried in air; yield, 13.73 g (brown powder): m.p. 50°-60° C.

Provenance & Evidence