Sciencemadness Discussion Board

synthesis of 2-aminobenzenesulfonamide

amrhamed2 - 29-2-2008 at 05:44

I would like to know the method of synthesis of this compound

[Edited on 29-2-2008 by amrhamed2]

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Nicodem - 29-2-2008 at 07:20

Show us first you did a literature search yourself. From your post one could get an impression you did not put any effort whatsoever in finding the answer yourself.

amrhamed2 - 29-2-2008 at 07:40

I really searched using scifinder
I could find it could be prepared from 2-nitrobenznesulfonamide reduction...Tetrahedron Letters, 42(33), 5601-5603; 2001

The problem is that I didn't find a method to prepare 2-nitrobenzensulfonamide ....I know it is commercially available but I want to know the synthesis method

[Edited on 29-2-2008 by amrhamed2]

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Nicodem - 29-2-2008 at 08:15

Well, Beilstein is barrely more informative. The only retrosynthetic route it gave was:


There must be an easier route since otherwise it would not be as cheap as 6 EUR/g if the producers used the above never ending synthesis.

[Edited on 29/2/2008 by Nicodem]

Sauron - 29-2-2008 at 08:16

I suggest you go to the forum library and download Vogel's Practical Organnic Chemistry

See the chapters on aromatic nitration and aromatic sulfonation.

Also further along see orthanilic acid (2-aminobenzenesulphonic acid).

The compound you are asking about is simply the amide frm of orthanilic acid.

Is this a homework assignment? Sounds rather like a pedagogical problem.

In that instance no one here wants to do your homework for you.

Should you actually be trying to make this, be aware that the key precursor, o-nitrochlorobenzene is a very toxic material readily absorbed through the skin and by inhalation. So I hope you have a fume hood, gloves and goggles and sufficient training to avoid hurting yourself.

Once you follow the Org.Syn. preps to the 0-nitrobenzenesulfonyl chloride stage, it's time to make the sulfonadmide before proceeding to reduce the nitro group.

A different reducing agnt might serve you better in this instance.

[Edited on 29-2-2008 by Sauron]

amrhamed2 - 29-2-2008 at 08:45

Quote:



  • 2-nitrobenzenesulfonamide is prepared from 2-nitrobenzenesulfonyl chloride:

    Rozentsveig, I. B.; Levkovskaya, G. G.; Rybalova, T. N.; Mirskova, A. N.; Russ. J. Org. Chem., 37(1), 2001, 87-92. (Zh. Org. Khim., 37(1) 2001, 97-102.)

    Ruosteuso, P.; Haekkinen, A.-M.; Mattila, T.; Magn. Reson. Chem., 25, 1987, 189-193.

    Limpricht; Justus Liebigs Ann. Chem., 177, 1875, 62.




    [Edited on 29/2/2008 by Nicodem]


    • Thanks for those references Nicoderm....

    To Sauron ....I will try using orthanilic acid as u suggest ...have u any comment or suggestion about a procedure which gives good yield

    Sauron - 29-2-2008 at 23:18

    The conversion of a sulfonic acid to a sulfonamide is I believe well illustrated in Vogel. It is quite classical, as these compounds formerly were of great importance as antibitics.

    The benzenesulfonyl chloride is more reactive with ammonia than the benzenesulfonic acid itself. Which is why I suggested that you prepare the amide at that stage prior to reduction of the nitro group.

    This really is textbook stuff. For comparative procedures you can search Org.Syn foir SO2-OH to SO2-NH2 under Reaction Types, or see Comprehensive Organic Functional Group Transformations, by Katritzsky et al, the multivolume set of ebooks has been available for some time in References.