Process for production of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C548S250000

Reexamination Certificate

active

10573034

ABSTRACT:
The present invention relates to a process for producing an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2):the process comprising the step of reacting in an organic solvent a tertiary amine, a 2,2,2-trifluoro-N-arylacetamide represented by Formula (1):and at least one member selected from the group consisting of phosphorus oxychloride and diphenyl chlorophosphate; and a process for producing a 1-aryl-5-(trifluoromethyl)-1H-tetrazole represented by Formula (4):the process comprising the step of reacting in an aromatic hydrocarbon solvent, in the presence of an amine salt, an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2) shown above and an azide.

REFERENCES:
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Smith, Peter A.S. et al., “The Thermal Breakdown of Diaryltetrazoles”,J. Am. Chem. Soc., vol. 80, pp. 4647-4654, 1958.
Vaughan, John et al., “The Effect of Some Substituents on the Thermal Breakdown of Diaryltetrazoles”,J. Org. Chem., vol. 23, pp. 1909-1912, 1958.
Kadaba, Pankaja K., “Protic-Dipolar Aprotic Solvents in 1,3-Cycloaddition Reactions.”Synth. Commun., vol. 1, pp. 1-5, 1971.
Padwa, Albert et al., “Synthetic Approaches Toward the Bi (2H-azirine) System”,J. Org. Chem., vol. 44, No. 19, pp. 3281-3287, 1979.
Xiao, Jingbo et al., “Synthesis of Trifluoromethyltetrazoles Via Building Block Strategy”,J. Fluorine Chem., vol. 99, pp. 83-85, 1999.
Tamura, Kenji et al., “One-Pot Synthesis of Trifluoroacetimidoyl Halides”,J. Org. Chem., vol. 58, pp. 32-35, 1993.
Shchegel'skii, V.F. et al., “Synthesis and Anticholinesterase Activity of Flourine-Containing Aryliminophosphonates and Phosphinates”,Pharmaceutical Chemistry Journal, 30(11), pp. 690-692, 1996.
Xiao, Jingbo et al., “Synthesis of Trifluoromethyltetrazoles via Building Block Strategy”,Journal of Fluorine Chemistry, 99(1), pp. 83-85, 1999.

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