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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 18
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Original Articles

An Improved Procedure for the Large Scale Preparation of 2-Chloro-4,6-dimethoxy-1,3,5-triazine

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Pages 3491-3494 | Received 31 Mar 1996, Published online: 21 Aug 2006

References

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  • Weber , A. J.M. , Huysmans , W. G.B. , Mijs , W. J. , Bovee , W. M.M.J. , Smidt , J. and Vriend , J. 1978 . Recl. Trav. Chim. Pays-Bas , 97 : 107
  • Menicagli , R. , Malanga , C. and Peluso , P. 1994 . Synth. Commun. , 24 : 2153
  • Potassium bicarbonate functioned equally well in the reaction Other bases such as sodium, potassium, and cesium carbonate gave increased levels of 2 and/or lower yields of 1
  • The reaction mixture was analysed using a Hewitt Packard 5980 capillary GC with an DB-1 crosslinked methyl-silicon column, 30m × 0.25mm × −.25μm, at a column temperature of 250° C and flow rate of 1.7 mL/min. The retention times are as follows: 2,4-dichloro-6-methoxy-1,3,5-triazine: 2.5 min; 2-chloro-4,6-dimethoxy-1,3,5-triazine: 3.0 min; 2,4,6-trimethoxy-1,3,5-triazine: 3.4 min
  • The endpoint of this reaction is defined as the time at which >97% conversion of the intermediate 2,4-dichloro-6-methoxy-1,3,5-triazine to CDMT has occurred. There is no residual cyanuric chloride
  • The conversion of cyanuric chloride to 2,4-dichloro-6-methoxy-1,3,5-triazine is accompanied by an exotherm. This appears to start at around 20° C and facilitates the warm-up to 35° C

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