Dissertation > Industrial Technology > Chemical Industry > Basic Organic Chemistry Industry > The production of heterocyclic compounds > Containing five pairs or more different atoms of heterocyclic > Between the two nitrogen -mao ( imidazole) and its derivatives

Study on the Synthesis Process of 2-Butyl-4-chloro-5-formy-limidazole

Author YuZhangSen
Tutor HuWangMing;ZhangWeiXing
School Zhejiang University
Course Chemical Engineering
Keywords 2-butyl-4-chloro-5-formy-limidazole Pinner Vilsmeier reagent chroloformylation
CLC TQ252.3
Type Master's thesis
Year 2010
Downloads 195
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2-Butyl-4-chloro-5-formy-limidazole is A key intermediate of Losartan. It was synthesized from valeronitrile by Pinner reaction, neutralization by CH3ONa, amination and Vilsmeier reaction with POCl3 and DMF. The suitable technical conditions for synthesizing the target compound were investigated in detail. The results were as follows:1. The suitable technical conditions for synthesizing methyl pentanimidate were:the mole ratio of valeronitrile, methanol and HCl 1:1.3:1.4, venting HCl at 0℃for 2 hours, holding reaction temperature 15℃for 12 hours, neutralized at 0℃. Then 0.932 yield of methyl pentanimidate was obtained.2. The suitable technical conditions for synthesizing (pentanimidoylamino)acetic acid were: the mole ratio of glycine and valeronitrile 1:1, the temperature 20℃, the reaction time 2 hours. Then 0.842 yield of (pentanimidoylamino)acetic acid was obtained.3. We substituded CH3ONa for NaOH to neutralize hydrochloride to get methyl pentani-midate. And then the synthesis route was simplified:methyl pentanimidate getted above can directly react with glycine without further purification and the yield was increased.4. The suitable technical conditions for synthesizing 2-Butyl-4-chloro-5-formy-limidazole by Vilsmeier reaction were:the mole ratio of (pentanimidoylamino)acetic acid, POC3 and DMF 1:2.8:3.0, adding DMF at 60℃, holding reaction temperature 100℃for 2 hours. Then 0.83 yield of 2-Butyl-4-chloro-5-formy-limidazole was obtained. The total yield was increased from 55% up to 69%.5. We investigated the effect of toluene’s reuse times on 2-Butyl-4-chloro-5-formy-limidaz-ole’s yield and how to deal with the byproduct HCl and the waste water containing H3PO4.

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