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Phenylbromethylbenzenesulfonamid and phenylbromethylamin by Carl Leopold von Ende, 1893

Phenylbromethylbenzenesulfonamide and Phenylbromethylamin by Carl Leopold von Ende, 1893, Page 15

[page]14.[/page]

the base NHRR[subscript]1[/subscript] . First prepare the benzene-sulfonamid C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * NHR[subscript]1[/subscript] which is best done by benzenesulfonating the primary amin base NH[subscript]2[/subscript]R[subscript]1[/subscript] . This sulfonamid is dissolved in dilute alkali with the addition of a little alcohol, and is then treated with the halogen alkyl RCl and warmed on the waterbath for several hours. The sulfonamid C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * N[branch1]R[/branch1][branch2]R[subscript]1[/subscript][/branch2] thus formed, needs only to be split up with concentrated HCl at a temperature of 150 degrees, to obtain the chlorhydrate of the mixed secondary base.

 [underlined]Experimental[/underlined]

     The following are the steps for preparing from sodiumbenzenesulfonate, phenylbromethylbenzene-sulfonamid and from it phenylbromethylamin

(1)  C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript]ONa + PCl[subscript]5[/subscript] = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * Cl + POCl[subscript]3[/subscript] + NaCl

[? ? + ? yielding?] Benzenesulfochlorid [? + ? + sodium chloride ?]

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[page]14.[/page] the base NHRR[subscript]1[/subscript] . First prepare the benzene-sulfonamid C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * NHR[subscript]1[/subscript] which is best done by benzenesulfonating the primary amin base NH[subscript]2[/subscript]R[subscript]1[/subscript] . This sulfonamid is dissolved in dilute alkali with the addition of a little alcohol, and is then treated with the halogen alkyl RCl and warmed on the waterbath for several hours. The sulfonamid C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * N[branch1]R[/branch1][branch2]R[subscript]1[/subscript][/branch2] thus formed, needs only to be split up with concentrated HCl at a temperature of 150 degrees, to obtain the chlorhydrate of the mixed secondary base. [underlined]Experimental[/underlined] The following are the steps for preparing from sodiumbenzenesulfonate, phenylbromethylbenzene-sulfonamid and from it phenylbromethylamin (1) C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript]ONa + PCl[subscript]5[/subscript] = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * Cl + POCl[subscript]3[/subscript] + NaCl [? ? + ? yielding?] Benzenesulfochlorid [? + ? + sodium chloride ?]