[CONTRIBUTIONFROM
THE
KODAKRESEARCH LABORATORY I
ADDENDUM TO “THE IDENTIFICATION OF AROMATIC SULFONIC ACIDS CONTAINING AN AMINO GROUP” (1) C. F. H. ALLEN
AND
J. VAN ALLAN
Received July $8, 19G
A few years ago we described a procedure for the identification of aromatic amine sulfonic acids, particularly useful for securing solid derivatives having melting points in a convenient range (1). The melting points of a few more addiTARLE I PROPERTIES OF CERTAINSUBSTITUTED CHLOROBENZENESULFONAMIDES ANALYSIS AMXDE
Y.P.
1,2-Dimethyl-6-chlorobenzene-3-sulfonamide5 1,2-Dimethyl-4-chlorobenzene-5-sulfonamide 1,3-Dimethyl-4-chlorobenzened-sulfonamide 1,3-Dimethyl-5-chlorobenzene-2-suIfonamide 1 4-Dimethyl-2-chlorobenzene-5-sulfonamide 1-Ethyl-4-chlorobenzene -5-sulfonamide 4-t-Amyl-1-chlorobenzene -2-sulf onamide 4-Methoxy-1-chlorobenzene-2-sulfonamide 3-Methoxy-1-chlorobenzene-4-sulf onamide 2-Methoxy-1-chlorobenzene-4-sulfonamide 2-E thoxy-1-c hlorobenzene-4-sulf onaniide )
“c.
198 209 b 159 144 189” 122 137 148 168 124 136
Calc’d, %N
Found, %N
6.4
6.6
6.4 6.4 6.4 6.4 5.4 6.3 6.3 6.3 6.0
6.3 6.4 6.4 6.5 5.6 6.3 6.3 6.3 5.9
a We wish to acknowledge the assistance of Dr. Tiehler of Merck and Company, who furnished us with the crude nitro-o-xylenes. Kriiger (2) chlorinated the crude mixture resulting from the sulfonation of o-xylene, and separated the barium salts by fractional crystallization. He gave 199”for the melting point of the 6-chloro, and 209” for the 5-chloro derivatives. Wahl (3) gives m.p. 185’.
tional chlorobenzenesulfonamides which supplement this list have been accumulated during the course of our work. Their properties are given in Table I. The amine sulfonic acids are those of the more frequently encountered amines. ROCHESTER, Tu’. Y . REFERENCES (1) ALLENAND FRAME, J . Org. Chem., 7,15 (1942). (2) KRUGER,Ber., 18, 1757 (1885). (3) WAHL,Ann. Chim. [ l l ] 6 , 16 (1936).
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