The Preparation of Some Amino Sulfonamides

Miller, Ellis; Sprague, James M.; Kissinger, L. W.; McBurney, Lane F.

doi:10.1021/ja01865a053

Cited by 54 publications

(29 citation statements)

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“…[39] Another example is the hydrogenation of cyanopropylsulphonamide to 4-amino-1-butanesulphonamide but PtO 2 was used as the catalyst because the reaction with Pd/C was too slow. [40] CH 3 COOH has also successfully been used for this purpose. Hydrogenation of benzonitrile in CH 3 COOH over Pd on BaSO 4 gave over 80% yield of benzylamine.…”

Section: Effect Of the Addition Of Acidsmentioning

confidence: 99%

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

Gomez

Peters

Maschmeyer

2002

Advanced Synthesis & Catalysis

517

238

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This review deals with two of the most commonly used methods for the preparation of amines: the reductive amination of aldehydes and ketones and the hydrogenation of nitriles. There is a great similarity between these two methods, since both have the imine as intermediate. However, due to the high reactivity of this intermediate, primary, secondary and/or tertiary amines are obtained (often simultaneously). The relation of the selectivity to different substrate structures and reaction conditions is briefly summarised, the main focus being on the catalyst as it is the most significant factor that governs the selectivity. Different mechanisms are discussed with the view to correlate the structure of the catalyst and, more particularly, the nature of the metal and the support with selectivity. The crucial point is the presumed location of the condensation and hydrogenation steps.

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Section: Effect Of the Addition Of Acidsmentioning

confidence: 99%

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

Gomez

Peters

Maschmeyer

2002

Advanced Synthesis & Catalysis

517

238

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“…Through a soln. of the nitrile 2 (10 mmol) [1] [12] [13] in anh. MeOH (40 ml) containing MeONa (0.1 mol) and freshly prepared Raney Ni (1.0 g) [14], O 2 -free N 2 gas was bubbled for 10 -15 min.…”

Section: Experimental Partmentioning

confidence: 99%

Novel Synthesis of Mafenide and Other Amino Sulfonamides by Electrochemical Reduction of Cyano Sulfonamides

Lateef

Mohan

Rudraraju

et al. 2006

Helvetica Chimica Acta

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Both aliphatic and aromatic amino sulfonamides such as mafenide (1a) were synthesized in good yields (80 -86%) by direct electrochemical hydrogenation of the corresponding nitriles in an undivided cell containing a Ni cathode, a Pt anode, and Raney Ni as catalyst ( Table 1). The reaction can be performed without external supply of pressurized gas by in situ generation of H 2 . Slightly elevated temperatures (458) and low current densities (10 mA/cm 2 ) are favorable conditions for this type of electrochemical nitrile hydrogenation. Our synthetic protocol does not require high-pressure equipment or chemical hazards, is environmentally very friendly, and more economical than traditional methods. The concentration of adsorbed HC radicals on the catalyst surface can be easily controlled by adjusting the electric potential, which may lead to improved product selectivity and, at the same time, reduces the risk of explosion and fire.

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“…Hartung found in 1928 that it is possible to obtain the primary amine, without contamination from the secondary amine, by working in an alcoholic HCl solution and isolating the primary amine as the ammonium salt. [40] CH 3 COOH has also successfully been used for this purpose. [38] The same method was used for the inhibition of secondary amines in the Pd/C-catalysed hydrogenation of ocyanobenzenesulphonamide to o-aminomethylbenzenesulphonamide (Scheme 11).…”

Section: Effect Of the Addition Of Acidsmentioning

confidence: 99%

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

2003

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Dedicated to Professor Roger A. Sheldon on the occasion of his 60th birthday.Abstract: This review deals with two of the most commonly used methods for the preparation of amines: the reductive amination of aldehydes and ketones and the hydrogenation of nitriles. There is a great similarity between these two methods, since both have the imine as intermediate. However, due to the high reactivity of this intermediate, primary, secondary and/or tertiary amines are obtained 6 Conclusions

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The Preparation of Some Amino Sulfonamides

Cited by 54 publications

References 0 publications

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

Novel Synthesis of Mafenide and Other Amino Sulfonamides by Electrochemical Reduction of Cyano Sulfonamides

The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control

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