Hydrochloric Acid → 1(3H)-Isobenzofuranone, 3-[2,4-bis(dimethylamino)phenyl]-4,5,6,7-tetrachloro-3-[4-(diethylamino)-2-methylphenyl]-

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Reaction Conditions

Reaction Steps

A mixture of 2-(2-methyl-4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (22.4 g.), N,N,N',N'-tetramethyl-m-phenylenediamine (8.20 g.) and acetic anhydride (75 g.) was heated (to 95° C.) during one to two hours, then refluxed with dilute hydrochloric acid (32 g. concentrated hydrochloric acid plus 160 ml. water) during one and one-half hours. The resulting mixture was poured into water and the pH was adjusted. Recrystallization of the resulting product from toluene afforded 3-(2,4-bis(dimethylamino)phenyl)-3-(2-methyl-4-(diethylamino)phenyl)-4,5,6,7-tetrachlorophthalide (I: X= (CH3)2N, Y2 = CH3, Y4 = (CH3CH2)2N, Z4 = Z5 = Z6 = Z7 = Cl) (m.p. 236°-238° C.; after slurrying in acetone, 237°-239° C.).

Provenance & Evidence