The following fractions could not be identified by their physical properties nor by their derivatives: The fraction boiling at 210.5°had da, 0.9525, m"d 1.4878, a picrate and a phenyl urea melting at 202 and 221 °, respectively.Anal. Caled, for ethyl-di-(2-aminoethyl)-amine: N, 32.1; 1°amine N, 21.4; N of phenyl urea 18.9. Found: N, 32.1; 1°amine N, 21.4; N of phenyl urea, 18.3. Specific dispersion did not indicate unsaturation. MR caled., 41.1; found, 39.8. The fraction boiling at 233.5°had dat 0.997, n%D 1.5098 and a picrate decomposing at 208°.Anal. Caled, for l-[N-(2-aminoethyl)-2-aminoethyl]pyrroline: N, 27.0; 1°amino N, 9.00. Found: N, 26.9; 1°amino N, 9.00. The double bond was indicated by its specific dispersion of 155 instead of the usual 120. MR caled. 47.9; found: 46.5.
AVArylaminomethyl aryl sulfides and l,3,5-triaryI-l,5-dithia-3-azapentanes have been prepared by condensing primary aromatic amines with formaldehyde and thiophenols. A-Methylanilines condense with formaldehyde and thiophenols to form M-methykA-arylaminomethyl arjd sulfides.Two arylaminoethyl aryl sulfides were prepared by condensing /3-chloroethylaniline with the sodium salt of the thiophenol.Basicities of these arylaminoalkyl aryl sulfides have been related to (a) the presence of electrophilic substituents attached to the aryl groups and (b) the number of carbon atoms separating the nitrogen and sulfur atoms.Recently Grillot et at.1 have demonstrated that the thiophenols condense with secondary aliphatic amines and formaldehyde to form dialkylaminomethyl aryl sulfides similar in structure to the dialkylaminomethyl alkyl sulfides prepared by McLeod and Robinson2 by condensing aliphatic mercaptans with aliphatic amines and formaldehyde. The formation of these aminomethyl aryl sulfides was somewhat surprising, since phenols condense with secondary aliphatic amines and formaldehyde to form ortho and para substituted dialky laminomethylphenols.3 Although aromatic amines generally react with more sluggishness in the Mannich reaction than the corresponding aliphatic amines, iV-methylaniline, Ar-methyl-p-anisidine, and A-methyl-pnitroaniline react with thiophenols and formaldehyde according to the following equation: MeNHAr + ECHO + Ar'SB ->-Ar(Me)NCHiSAr' + E20to give moderately stable crystalline M-methyl-AT-ary laminóme thy 1 aryl sulfides.
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