1,1'-Carbonyldiimidazole → Benzeneacetamide

Participants

Reaction Steps

A solution of 4.23 g of 3,4-dichlorophenylacetic acid in 200 ml of methylene chloride was treated at 0° with 3.35 g of carbonyldiimidazole. The mixture was stirred for 40 min. Then, 2.86 g (0.0159 mol) of the (+) amine from the resolution which was previously described in Part D, above, was added. The mixture was stirred for 24 hr and partitioned with saturated aqueous sodium bicarbonate. The organic phase was dried and concentrated to yield 4.93 g of the named (-)-benzeneacetamide product which had an [α]D25 -24° (6.75 mg/ml in methanol). The product was dissolved in a minimum volume of methanol and treated with 1.48 g of maleic acid which had been dissolved in a minimum volume of methanol and the mixture was diluted with diethyl ether. The resultant crystals were filtered to yield 5.02 g of the named salt product, mp 167°-169°, [α]D25 -29.7° (10.0 mg/ml in methanol).

Provenance & Evidence