Dimethylformamide → 8-[4-Chloro-N-(4-methoxyphenyl)-benzamido]-caprylic acid methyl ester

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Reaction Steps

As described in example 1(a), the reaction is carried out with 130.7 g (0.5 mol) of 4-chloro-N-(4-methoxyphenyl)-benzamide, 24.5 g (1 mol) sodium hydride, 700 cc. of dimethylformamide and 118.5 g (0.5 mol) of 8-bromocaprylic acid methyl ester. Reaction time and reaction temperature: 5 hours at 80° C., thereafter 12 hours at 100° C. The reaction mixtures are further processed as described in example 1(a). The crude product is dissolved in 300 cc. of ether. After standing for a prolonged period, the unreacted 4-chloro-N-(4-methoxyphenyl)-benzamide separates by crystallisation and is filtered off. The solvent is partly distilled off and the resulting oily crude product (181 g) is separated. 125 g are used in the next step without further purification, the remainder (56 g) is purified chromatographically on silicic acid using chloroform as eluant.

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