1,1'-Carbonyldiimidazole → Benzeneacetamide

Participants

Reaction Steps

In a similar manner, 4.40 g of 3,4-dichlorophenylacetic acid, 3.47 g of carbonyldiimidazole and 2.97 g of the (-) amine from Part D, above, were reacted to yield the above-named (+)-benzeneacetamide product. This product was chromatographed on silica gel (2% methanol (which was saturated with ammonia gas)/98% ethyl acetate) to yield 3.22 g of pure benzeneacetamide product, [α]D25 +34° (8.2 mg/ml in methanol). This benzeneacetamide product was treated with 1.011 g of maleic acid in methanol and the mixture was diluted with diethyl ether to yield 3.56 g of the above named product salt, mp 174°-175° C., [α]D25 +35.3° (10.0 mg/ml in methanol).

Provenance & Evidence