RE: ORGLIST:Help wanted on synthesis!

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From: Yuehui Zhou (yuehuizhou$##$hotmail.com)
Date: Sat Jun 26 2004 - 01:50:47 EDT


Weiqiang,

Acetic acid instead of KOH may help the reaction. The react is involved with an iminium species as electrophile. Water should be avoided since it's unfavorable for the formation of the imine. You may try to run the reaction by refluxing in acetic acid.

Y. Zhou

>From: <tlong@dicp.ac.cn>
>Reply-To: <tlong@dicp.ac.cn>
>To: <everybody@orglist.net>
>Subject: ORGLIST:Help wanted on synthesis!
>Date: Wed, 23 Jun 2004 21:11:55 +0800
>
>everybody艇挫
>
>Anyone can give some help on the synthesis of 3,5-dimethyl-4-(ethylamino)methylpyrazole from the literature:
>Gloria esquius, Josefina Pons etc, J.Organomet.Chem.605(2000)226-233.
>
>Method:3,5-dimethylpyrazole (1.00g,16mmol),paraformaldehyde(0.48g,16mmol),KOH(0.90g,16mmol) and amine(ethylamine 70% in water,1.20g,20mmol) were dissolved in 50ml of water and refluxed for 48h. The mixture was extracted with CHCl3 and dried with anhydrous MgSO4. The solid was separated by filtration and the colerless filrtate was concentrated to dryness in vacuo.
>The commpound was obtained as a white solid.
>But I try to sythesize the compound by reflexing at 120≧ and don't obtain it. The material was not almostly reacted. The other conditions was the same to the literature.
>Can someone give me some suggistions of synthesis procedure or a modified method?
>
>Thanks
>
>
>        
>**********************************************
>weiqiang tan
>Group 203
>Dalian Institute of Chemical Physics
>Chinese Academy of Sciences
>457 Zhongshan Road, Dalian 116023
>P. R. China
>Tel: +86-411-84379551
>E-mail: tlong@dicp.ac.cn
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