Effective process for the production of 1,2,3-triazoles
AssigneeSynphar Laboratories, Inc.
InventorsInder P. Singh, Paul Spevak, Bhupinder Palak, Samuel Amedjo, Ronald J. Micetich
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Abstract
A high purity triazole is obtained by the reaction of a hydrazide of the general formula II and glyoxal followed by the treatment of the intermediate of general formula IV with ammonia. The total process is done in one pot and does not require the isolation of the intermediate IV. The triazole (I) is isolated by distillation. Synthesis of various N.sub.1 -substituted triazoles is also described following the same procedure.
Claims13
A method of producing 1,2,3-triazole, N.sub.1 -alkyl 1,2,3-triazole or aryl 1,2,3-triazole comprising
- reacting hydrazides of the formula II
- RNHNH.sub.2 (II),
- with glyoxal, and ammonia or an appropriately substituted amine,
- wherein R is R'CO or R'SO.sub.2 in which R' is a lower alkyl which is unsubstituted or substituted with halogens, or R' is a phenyl group which can be further substituted with chloro, fluoro, bromo, nitro, lower alkyl or lower alkoxy.
A method of producing 1,2,3-triazole comprising
- a) adding a solution of p-toluene sulfonyl hydrazide to a solution of glyoxal in the presence of acetic acid, and
- b) subsequently adding of NH.sub.3 gas.
A method of producing 1,2,3-triazole comprising adding NH.sub.3 gas to a mixture of p-toluene sulfonyl hydrazide and glyoxal in the presence of acetic acid.
A method for the production of 1,2,3-triazole comprising
- a) adding a glyoxal solution to a solution of p-chlorobenzene sulfonyl hydrazide in the presence of acetic acid, and
- b) subsequently adding NH.sub.3 gas.
A method for the production of 1,2,3-triazole comprising
- a) adding glyoxal solution into a solution of m-nitro benzoyl hydrazide in the presence of acetic acid, and
- b) subsequently adding NH.sub.3 gas.
A method for the production of 1,2,3-triazole comprising
- a) adding solid p-toluene sulfonyl hydrazide into a stirred solution of glyoxal and acetic acid in methanol, and
- b) subsequently adding ammonia gas.
A method of producing N.sub.1 -benzyl-1,2,3-triazole, N.sub.1 -ethyl-1,2,3-triazole, or N.sub.1 -cyclopropyl-1,2,3-triazole comprising reacting glyoxal, p-toluene sulfonyl hydrazide, and an appropriately substituted amine to give corresponding N.sub.1 -substituted-1,2,3-triazole.
Dependencies are inferred from the claim text.