Synthesis and structure elucidation of 3-methoxy-1-methyl-1H-1,2,4,-triazol-5-amine and 5-methoxy-1-methyl-1H-1,2,4,-triazol-3-amine |
| |
Authors: | T P Selby G E Lepone |
| |
Institution: | Agricultural Chemicals Department, Experimental Station, E. I. du Pont de Nemours and Co., Inc., Wilmington, Delaware 19898 |
| |
Abstract: | Previously it was shown that condensation of dimethyl N-cyanodithioimidocarbonate ( 1a ) with methylhydrazine gave predominantly 1-methyl-5-methylthio-1H-,2,4-triazol-3-amine ( 2 ), which was initially identified erroneously as the regioisomer l-methyl-3-methylthio-1H-1,2,4-triazol-5-amine ( 3 ). We have found that reaction of dimethyl N-cyanoimidocarbonate ( 1b ) with methyl hydrazine affords a high yield of 3-methoxy-1-methyl-1H-1,2,4-triazol-5-amine ( 4 ) rather than the regioisomer 5-methoxy-1-methyl-1H-1,2,4-triazol-3-amine ( 5 ). The structure assignment of 4 was confirmed by X-ray crystallographic analysis of the benzenesulfonyl isocyanate adduct 7 . Triazole 5 was obtained after reacting dimethyl N-cyanothioimidocarbonate ( 1c ) with methylhydrazine. |
| |
Keywords: | |
|
|