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Phenylbromethylbenzenesulfonamid and phenylbromethylamin by Carl Leopold von Ende, 1893

Phenylbromethylbenzenesulfonamide and Phenylbromethylamin by Carl Leopold von Ende, 1893, Page 16

[page]15.[/page]

(2)  C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * Cl + 2C[subscript]6[/subscript]H[subscript]5[/subscript] * NH[subscript]2[/subscript] = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * NH * C[subscript]6[/subscript]H[subscript]5[/subscript] + C[subscript]6[/subscript]H[subscript]5[/subscript]N[?*?]H[subscript]2[/subscript] * HCl

[??? + ?] Anilin [?yielding?] Benzenesulfanilid [?+ ?]

(3)  C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * N[? * ?]H * C[subscript]6[/subscript]H[subscript]5[/subscript] + NaOH + BrC[subscript]2[/subscript]H[subscript]4[/subscript]Br = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * N[branch1]C[subscript]6[/subscript]H[subscript]5[/subscript][/branch1][branch2]C[subscript]2[/subscript]H[subscript]4[/subscript]Br[/branch2] + NaBr + H[subscript]2[/subscript]O .

[?yielding?] Phenylbromethylbenzenesulfonamid.

(4)  C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript]N[branch1]C[subscript]6[/subscript]H[subscript]5[/subscript][/branch1][branch2]C[subscript]2[/subscript]H[subscript]4[/subscript]Br[/branch2] + H[subscript]2[/subscript]O + HBr = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * OH + [branch0]H[/branch0]N[branch1]H[/branch1][branch2]Br[/branch2][branch3]C[subscript]2[/subscript]H[subscript]4[/subscript]Br[/branch3][branch4]C[subscript]6[/subscript]H[subscript]5[/subscript][/branch4]

[? ? ? + water + ?] Hydrolizing with fuming HBr [?yielding ? + ?] Bromethylphenyl-ammoniumbromid.

     The last compound is the hydrobromid of the mixed secondary [?amin?] sought for.
     The sodiumbenzenesulfonate is prepared from benzene by treating it with chlorosulfonic acid and the precipitating with a saturated solution of NaCl. The flask with a long tube condenser, in which the operation was carried on, was kept cool by constantly shaking under a water tap. The sodiumbenzenesulfonate is purified and freed from the diphenylsulfone, formed at the same time, by dissolving in hot water, filtering,

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[page]15.[/page] (2) C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * Cl + 2C[subscript]6[/subscript]H[subscript]5[/subscript] * NH[subscript]2[/subscript] = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * NH * C[subscript]6[/subscript]H[subscript]5[/subscript] + C[subscript]6[/subscript]H[subscript]5[/subscript]N[?*?]H[subscript]2[/subscript] * HCl [??? + ?] Anilin [?yielding?] Benzenesulfanilid [?+ ?] (3) C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * N[? * ?]H * C[subscript]6[/subscript]H[subscript]5[/subscript] + NaOH + BrC[subscript]2[/subscript]H[subscript]4[/subscript]Br = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * N[branch1]C[subscript]6[/subscript]H[subscript]5[/subscript][/branch1][branch2]C[subscript]2[/subscript]H[subscript]4[/subscript]Br[/branch2] + NaBr + H[subscript]2[/subscript]O . [?yielding?] Phenylbromethylbenzenesulfonamid. (4) C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript]N[branch1]C[subscript]6[/subscript]H[subscript]5[/subscript][/branch1][branch2]C[subscript]2[/subscript]H[subscript]4[/subscript]Br[/branch2] + H[subscript]2[/subscript]O + HBr = C[subscript]6[/subscript]H[subscript]5[/subscript] * SO[subscript]2[/subscript] * OH + [branch0]H[/branch0]N[branch1]H[/branch1][branch2]Br[/branch2][branch3]C[subscript]2[/subscript]H[subscript]4[/subscript]Br[/branch3][branch4]C[subscript]6[/subscript]H[subscript]5[/subscript][/branch4] [? ? ? + water + ?] Hydrolizing with fuming HBr [?yielding ? + ?] Bromethylphenyl-ammoniumbromid. The last compound is the hydrobromid of the mixed secondary [?amin?] sought for. The sodiumbenzenesulfonate is prepared from benzene by treating it with chlorosulfonic acid and the precipitating with a saturated solution of NaCl. The flask with a long tube condenser, in which the operation was carried on, was kept cool by constantly shaking under a water tap. The sodiumbenzenesulfonate is purified and freed from the diphenylsulfone, formed at the same time, by dissolving in hot water, filtering,