One hundred thirty-eight grams (1 mole) of p-nitroaniline (East-man Technical grade) is dissolved in
370 cc. of boiling glacial acetic acid in a
2-l. three-necked flask provided with a
mechanical stirrer, a
reflux condenser, and a
dropping funnel. The burner is removed, and a mixture of
325 g. (2 moles) of iodine monochloride (Note
1) in
100 cc. of glacial acetic acid is added slowly from the
dropping funnel with rapid stirring during thirty minutes. Considerable heat is evolved. The mixture is heated on a rapidly boiling
water bath for two hours and then transferred to a
1-l. beaker and allowed to cool. The solidified mixture is treated with
100 cc. of glacial acetic acid and any hard lumps are crushed thoroughly with a
flat glass stopper (Note
2). The mixture is transferred to a
large Büchner funnel and filtered by suction, two
25-cc. portions of glacial acetic acid being used to wash the last of the crystals into the funnel. The dark mother liquor is removed as completely as possible by suction. The crystals are returned to the beaker, thoroughly stirred with
200 cc. of cold glacial acetic acid, and transferred to the
suction filter again. The beaker is rinsed with two
25-cc. portions of glacial acetic acid, and the crystals are sucked as dry as possible. The suction is shut off, and the crystals are wetted with
50 cc. of ether. The suction is again used to remove the
ether. The product is air dried to constant weight (about twenty-four hours). The yield of air-dried
diiodo-p-nitroaniline melting at
243–245° is
220–250 g. (
56–64 per cent of the theoretical amount) (Note
3).