ORGLIST: sulfonamide synth and alcohol protection

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From: Jason Smith (loggin1270$##$hotmail.com)
Date: Sat Aug 06 2005 - 08:14:29 EDT


I am looking for a procedure for creating a sulfonamide using
p-Acetamidobenzenesulfonyl chloride (ABS) and 1-amino-2-propanol and
3-aminopropanol. My obvious concern is reaction of the sulfonyl chloride
with the hydroxyl group. I would be very much appreciative of any
suggestions you may have.
Currently I have already rejected the use of allylamine.
    I thought of using a chlorotrialkylsilane however I would assume that
there is a high risk of the amine reacting with such a species and these
could not be easily seperated. I have investigated Dihydropyran however will
most likely not be able to wait for shipping and likewise for MEM chloride.
I am wondering perhaps if anyone has used the procedure using protonated
amines and 2-nitrobenzenesulfonyl chloride ( R. N. Salvatore et al.
tetrahedron 57 (2001), pg 7792) where the amine adds to S. This procedure is
described for monoalkylation of amine but i would curious to know if you
think it could be adapted for ABS.
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