Abstract
N-Lauroylsarcosine was synthesized by selective hydrolysis of N-lauroylsarcosinonitrile as shown in the previous paper.
The application of this reaction to other acylaminonitriles was studied with aminonitriles such as aminoacetonitrile, sarcosinonitrile and N-ethylaminoacetonitrile, and acyl groups studied were formyl, stearoyl, oleoyl, chloroacetyl and benzoyl.
It was found that in the case of acetyl- or longer chain acyl- aminonitrile the cyano group was selectively hydrolyzed with alkali or acid. The result was reversed in the case of formyl and chloroacetyl compound, that is, acyl group was selectively hydrolyzed with alkali or acid.
The dissociation constant ratios of these carboxylic acids to acetic acid are from 1.0 to 0.7 for acetic to caprylic acid and 3.6, 10.2 and 76.6 for benzoic, formic and chloroacetic acids respectively.
It is concluded that in the case where the ratio is 1.0 or less the cyano group is selectively hydrolyzed ; in the case with the ratio of 3.6 or so the cyano group is hydrolysed predominantly accompanied with acyl group hydrolysis ; and in the case with the ratio more than 10 the acyl group is selectively hydrolyzed. The steric effect of acyl group is minor compared with the dissociation constant effect of acyl group.
