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ChemicalBook CAS DataBase List 3-Amino-1,2,4-Triazole
61-82-5

3-Amino-1,2,4-Triazole synthesis

9synthesis methods
Amitrole is synthesized by condensing formic acid with aminoguanidine and can be purified by recrystallization from methanol.
-

Yield:-

Reaction Conditions:

with ammonia;aminoguanidine in methanol;N,N-dimethyl-formamide;toluene;

Steps:

9 PART II:

In this synthesis, the ester group of intermediate 33 is converted to a nitrile prior to alkylating a heterocycle (Part I) with this substituted benzyl element. Thus, reaction of ester 33 with ammonia in methanol, followed by dehydration of amide 34 produces nitrile 35. Benzylic bromination affords 36, which then may be reacted with the sodium salt of a heterocycle such as 5 in DMF to give an intermediate like 37. Finally, reaction of a nitrile like 37 with trimethylstannyl azide in refluxing toluene gives tetrazoles related to 38 as shown in Scheme II-9. STR57 The preparation of a derivative of Formula I analogous to tetrazole 38 (Scheme II-9) in which X is a methylene group, Y is a single bond and R12 is phenyl, is shown in Scheme II-11. In this synthesis, phenylacetonitrile is deprotonated with lithium bis(trimethylsilyl)amide and then alkylated with the tert-butyldimethylsilylether of p-hydroxymethylbenzyl bromide (preparation of bromide 39 is shown in Scheme II-10) to yield nitrile 40.

References:

US5264439,1993,A

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