Water → HCID 585597, compound

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Reaction Steps

Dissolve 2.0 g. (10 mmoles) of 1-adamantane carboxylic acid chloride in 20 ml. of ethyl ether and add to 3.0 ml. (32.9 mmoles) of aniline. Stir the mixture 15 minutes, then add 20 ml. of water and 25 ml. of ethyl acetate. Separate the layers and extract the aqueous layer several times with ethyl acetate. Combine the extracts and wash with 2N hydrochloric acid, saturated sodium bicarbonate solution, and water. Dry the extract over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from ethyl acetate to obtain the product of this example, m.p. 196°-199°C.

Provenance & Evidence