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Synthesis of 4‐amino‐3,5‐dinitro‐1 H ‐pyrazole using vicarious nucleophilic substitution of hydrogen
Author(s) -
Schmidt Robert D.,
Lee Gregory S.,
Pagoria Philip F.,
Mitchell Alexander R.,
Gilardi Richard
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380533
Subject(s) - chemistry , pyrazole , recrystallization (geology) , nucleophilic substitution , iodide , nucleophilic aromatic substitution , medicinal chemistry , organic chemistry , paleontology , biology
A novel synthesis of the title compound was achieved by direct animation using Vicarious Nucleophilic Substitution (VNS) methodology. Reaction of 1,1,1‐trimethylhydrazinium iodide with 3,5‐dinitropyrazole in DMSO produces 4‐amino‐3,5‐dinitro‐1 H ‐pyrazole as a 1:1 crystal solvate with DMSO. Recrystallization from water yields the monohydrated crystal. Recrystallization of the monohydrate from butyl acetate yields the compound in pure form.