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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 16
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Original Articles

FeCl3 · 6H2O-Catalyzed Acceleration of the Acylation of Sodium Azide with N-Acylbenzotriazoles

, , , &
Pages 2461-2467 | Received 22 Aug 2009, Published online: 14 Jun 2011
 

Abstract

Catalyzed by ferric chloride hexahydrate (FeCl3 · 6H2O), the acylation of sodium azide with N-acylbenzotriazoles was greatly accelerated in a mixed solvent of acetone and water. Thus, good to excellent yields of a variety of acyl azides were obtained at room temperature in a short time. Furthermore, because of the complete conversion of N-acylbenzotriazoles and the easy removal of the by-product, purification by column chromatography was no longer required, which made the protocol suitable for large-scale preparation.

ACKNOWLEDGMENT

We are grateful to the National Natural Science Foundation of China (No. 20802070) for financial support.

Notes

a All the runs were carried out with 1 mmol of N-benzoyl benzotriazole in 3 mL of the solvent, fresh sodium azide solution (3 mmol of sodium azide in 1 mL of water) and 5 mol% of FeCl3 · 6H2O.

b The conversion of N-benzoyl benzotriazole was determined by HPLC.

c The time required in the absence of FeCl3 · 6H2O as reported in Ref. [4].

a Yields were isolated yields and based on N-acylbenzotriazoles.

b The yields using the methods reported in Ref. [4] were listed in the parentheses.

c With 5 mol% of catalyst, incomplete conversion of 1d was observed, which would lead to the isolation of product 2c by column chromatography.

d Product 2q was determined by 1H NMR, but it was contaminated by 1q.

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