Acetic Anhydride → HCID 20523539, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5.20 g (0.01 mole) of 2-[(1-n-butyl-2-methyl-3-indolyl)carbonyl]-3,4,5,6-tetrachlorobenzoic acid, prepared in part A above, 2.0 g (0.012 mole) of N,N,N',N'-tetramethyl-m-phenylenediamine and five ml of acetic anhydride was warmed over a period of approximately forty minutes at 100° C. The reaction mixture was then cooled to ambient temperature, set aside overnight, rendered alkaline with 10 percent aqueous sodium hydroxide solution and extracted with benzene. Petroleum ether was slowly added to the separated benzene extract and the solid which slowly separated was collected by filtration and dried to obtain 3-[2,4-bis(dimethylamino)phenyl]-3-(1-n-butyl-2-methyl3-indolyl)-4,5,6,7-tetrachlorophthalide (Formula III: R°=R1 =R2 =R3 =Cl; R=R5 =CH3 ; R4 =N(CH3)2 ; R6 =(CH2)3CH3 ; Y1 =H), as white crystals having a melting point of 173°-175° C. The nuclear magnetic resonance spectrum was consistent with the structure; a maximum of 1770 cm-1 (C=O; s) appeared in the infrared spectrum; the spectrum showed a m/e peak at 617 (M+, 4 Cl).

Provenance & Evidence