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Phenylbromethylbenzenesulfonamid and phenylbromethylamin by Carl Leopold von Ende, 1893

Phenylbromethylbenzenesulfonamide and Phenylbromethylamin by Carl Leopold von Ende, 1893, Page 10

[page]9[/page]

The latter will first be formed in the reaction which takes place.

C[subscript]2[/subscript]H[subscript]3[/subscript]O * O * NH[subscript]4[/subscript] = C[subscript]2[/subscript]H[subscript]3[/subscript]O * NH[subscript]2[/subscript] + H[subscript]2[/subscript]O

4th by distillation of the fatty acids with potassium sulfocyanid

2C[subscript]2[/subscript]H[subscript]3[/subscript]O * OH + Cu * SK = C[subscript]2[/subscript]H[subscript]3[/subscript]O * NH[subscript]2[/subscript] + C[subscript]2[/subscript]H[subscript]3[/subscript]O * OK + COS

5th by hydrolizing the nitrites of the acids.

CH[subscript]3[/subscript] * Cu + H[subscript]2[/subscript]O = CH[subscript]3[/subscript] * CO * NH[subscript]2[/subscript]

Acetonitrite   [?+ water yielding?]   [?Acetarmid?]

     These methods given, do not give secondary and tertiary amids. They are obtained by heating the alkyl cyanids with acids or acid anhydrids to 200 degrees.

CH[subscript]3[/subscript] * Cu + CH[subscript]3[/subscript] * CO * OH = [branch1]CH[subscript]3[/subscript] * CO[/branch1][branch2]CH[subscript]3[/subscript] * CO[/branch2]NH

[?yielding?] Diacetamid.

CH[subscript]3[/subscript] * Cu + (CH[subscript]3[/subscript] * CO)[subscript]2[/subscript] = (CH[subscript]3[/subscript]CO)[subscript]3[/subscript]N

[??+?] Acetic anhydrid [?yielding?] Triacetamid

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[page]9[/page] The latter will first be formed in the reaction which takes place. C[subscript]2[/subscript]H[subscript]3[/subscript]O * O * NH[subscript]4[/subscript] = C[subscript]2[/subscript]H[subscript]3[/subscript]O * NH[subscript]2[/subscript] + H[subscript]2[/subscript]O 4th by distillation of the fatty acids with potassium sulfocyanid 2C[subscript]2[/subscript]H[subscript]3[/subscript]O * OH + Cu * SK = C[subscript]2[/subscript]H[subscript]3[/subscript]O * NH[subscript]2[/subscript] + C[subscript]2[/subscript]H[subscript]3[/subscript]O * OK + COS 5th by hydrolizing the nitrites of the acids. CH[subscript]3[/subscript] * Cu + H[subscript]2[/subscript]O = CH[subscript]3[/subscript] * CO * NH[subscript]2[/subscript] Acetonitrite [?+ water yielding?] [?Acetarmid?] These methods given, do not give secondary and tertiary amids. They are obtained by heating the alkyl cyanids with acids or acid anhydrids to 200 degrees. CH[subscript]3[/subscript] * Cu + CH[subscript]3[/subscript] * CO * OH = [branch1]CH[subscript]3[/subscript] * CO[/branch1][branch2]CH[subscript]3[/subscript] * CO[/branch2]NH [?yielding?] Diacetamid. CH[subscript]3[/subscript] * Cu + (CH[subscript]3[/subscript] * CO)[subscript]2[/subscript] = (CH[subscript]3[/subscript]CO)[subscript]3[/subscript]N [??+?] Acetic anhydrid [?yielding?] Triacetamid