Acetic Anhydride → 3,3-Bis(2,4-bis(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide

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Reaction Steps

A mixture of most of the 2-(2,4-bis(dimethylamino)-benzoyl)-3,4,5,6-tetrachlorobenzoic acid from part A of this example, N,N,N',N'-tetramethyl-m-phenylenediamine (0.82 g. plus 0.4 g.) and acetic anhydride was heated under reflux. Concentration of a toluene extract of the resulting product gave a tar, which was slurried in hexane, affording 3,3-bis(2,4-bis(dimethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X= Y2 = Y 4 = (CH3)2N, Z4 = Z5 = Z6 = Z7 = Cl) (m.p. 195°-197° C.).

Provenance & Evidence