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salt. Acidification of this salt then precipitates the sulfonamide of the primary amine. A secondary amine in the same reaction will directly form an insoluble sulfonamide. A tertiary amine will not react with the original reagent (benzene sulfonyl chloride) and will remain insoluble. After adding
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Tertiary amines are able to react with benzenesulfonyl chloride under a variety of conditions; the test described above is not absolute. The
Hinsberg test for amines is valid only when reaction speed, concentration, temperature, and solubility are taken into account.
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Amines serve as nucleophiles in attacking the sulfonyl chloride electrophile, displacing chloride. The sulfonamides resulting from primary and secondary amines are poorly soluble and precipitate as solids from solution.
168:"The systematic identification of organic compounds" 4th ed. by Ralph L. Shriner, Reynold C. Fuson, and David Y. Curtin. John Wiley & Sons, Inc., New York, 1956.
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For primary amines (R' = H), the initially formed sulfonamide is deprotonated by base to give a water-soluble sulfonamide salt (Na).
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Gambill, C. R. (1972). "Benzenesulfonyl chloride does react with tertiary amines. The
Hinsberg test in proper prospective".
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Tertiary amines promote hydrolysis of the sulfonyl chloride functional group, which affords water-soluble sulfonate salts.
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Ueber die
Bildung von Säureestern und Säureamiden bei Gegenwart von Wasser und Alkali
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48:. In this way the reaction can distinguish between the three types of amines.
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in 1890. In this test, the amine is shaken well with the
Hinsberg reagent (
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is a chemical test for the detection of primary, secondary and tertiary
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Chemical test to distinguish primary, secondary & tertiary amines
35:) in the presence of aqueous alkali (either KOH or NaOH). A
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dilute acid this insoluble amine is converted to a soluble
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Ueber die
Trennung der primären und secundären Aminbasen
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27:. The reaction was first described by
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188:Journal of Chemical Education
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176:and more recent editions.
158:10.1002/cber.190503801161
135:O. Hinsberg, J. Kessler:
125:10.1002/cber.189002302215
33:benzenesulfonyl chloride
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174:10.1002/jps.3030450636
142:Ber. Dtsch. Chem. Ges.
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39:will form a soluble
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19:The
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