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Preparation of 1-(1,5-dimethyl-1H-1,2,3-triazol-4-yl)ethanone oxime; 1-(1,5-dimethyl-1H-1,2,3-triazol-4-yl)ethanone oxime

SyntheticPage 473
DOI: 10.1039/SP473
Submitted Nov 14, 2010, published Nov 14, 2010
Yuri Shafran (Yuri.Shafran@mail.ru)
Reaction Scheme: Preparation of <span id="csm1290105414463" class="csm-chemical-name" title="1-(1,5-dimethyl-1H-1,2,3-triazol-4-yl)ethanone oxime">1-(1,5-dimethyl-1H-1,2,3-triazol-4-yl)ethanone oxime</span>

Chemicals Used

1-(1,5-dimethyl-1H-1,2,3-triazol-4-yl)ethanone
ethanol
hydroxylamine hydrochloride
triethylamine

Procedure

To a solution of 1.39 g (10.0 mmol) 1-(1,5-dimethyl-1H-1,2,3-triazol-4-yl)ethanone in 6 ml ethanol 0.69 g (10.0 mmol) hydroxylamine hydrochloride and 1.4 ml (10.0 mmol) triethylamine was added. Solution is warmed to boiling, volatiles were evaporated in vacuum. Residue was crystallized from water with charcoal to give1.23 g (80%) 1-(1,5-dimethyl-1H-1,2,3-triazol-4-yl)ethanone oxime.

Author's Comments

Carried out once, but seems to be reliable.

Data

MP 247oC. 1H NMR (DССl3): 2.22 (3H,s,Ме), 2.42 (3H,s,Me), 3.93 (3H,s,NMe), 10.99 (1H,s,=NOH). Found, %: C 46.4; H 6.5; N 36.8. C6H10N4O. Calc., %: C 46.7; H 6.5; N 36.3.

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Keywords: condensation, heterocyclic compounds, imine, ketones