From: Jacob Zabicky (zabicky$##$bgumail.bgu.ac.il)
Date: Sun Jun 23 2002 - 05:22:18 EDT
Hello George,
It's not clear whether you want 1,2- or 2,2-dialkylation of the
1-acylhydrazine. At any rate, the following references to N-alkylation
using dimethyl sulfate and to the alkylation of hydrazides--all very old
stuff--may be useful:
1. F. Ullmann and P. Wenner, Chem. Ber. 33, 2476 (1900).
2. F. Ullmann and P. Wenner, Annalen 327, 120 (1903).
3. J. Foeldi, Chem. Ber. 55, 1535 (1922).
4. J. Ferns and Z. Lapworth, J. Chem. Soc. 101, 281 (1912).
5. H. Paulsen and D. Stoye, in "The Chemistry of Amides", (J. Zabicky,
ed..), Interscience Publishers, London, 1970, pp. 515-600.
All the best,
Jacob
At 20:15 19/06/2002, Merlin wrote:
>Colleagues:
>
>Has anyone performed a DImethylation on a hydrazIDE?
>
>We currently have utilized and concoction of the starting hydrazide with
>MeI, 60% NaOH, and a PTC (TBAI) in toluene.
>
>Yields generated were averaging around 80%.
>
>Thing is, this won't work on scale up (2kg and greater).
>
>Has anyone performed similar DImethylations on hydrazIDES?
>
>We are thinking on using Dimethyl sulfate.
>
>Current searches on Crossfire & SciFinder have given very little
>information.
>
>Any feedback (comments, literature sources) would be greatly appreciated.
>
>Thank you in advance.
>
>Cheers!
>--
>George D. 'Merlin' McCallion
>Associate Research Scientist
>Chemical Development
>Sanofi-Synthelabo Research
>25 Great Valley Parkway
>Malvern, PA 19355
>United States
>
>Office: 610.889.6294
>Fax: 610.889.6367
>E: George.McCallion$##$sanofi-synthelabo.com
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Prof. Jacob Zabicky
Institutes for Applied Research
Ben-Gurion University of the Negev Private: POB 12366, Beer-Sheva 84863
POB 653, Beer-Sheva 84105, ISRAEL Tel. +972-8-6496792
http://profiler.bgu.ac.il/site/main.cfm
Tel. +972-8-6461271/6461062/6472754
Fax. +972-8-6472969
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