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63749108267
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note
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Ethyl bromide (21.8 g, 0.2 mol) was added with stirring to a suspension of salt 5 (13.6 g, 0.1 mol) in ethanol (115 mL) at 40 °C. The reaction mixture was heated gradually to 80 °C and stirred for 10 h at this temperature. After cooling to room temperature, the resulting precipitate was filtered off and the filtrate was evaporated under vacuum. The residue was dissolved in dichloromethane. The resulting solution was washed with 3% aqueous sodium bicarbonate solution, water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under vacuum giving a crude mixture of triazoles 6-8 (12.4 g, 87%). Vacuum distillation afforded a mixture of isomers 7 and 8 (bp 112-118 °C/18-20 mm Hg, 6.9 g, 49%). Triazole 6 (5.1 g, 36%) was isolated by recrystallization of the distillation residue from ethanol. Mp 78.5-79 °C.
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12
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84943402961
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Katritzky A.R., and Rees C.W. (Eds), Pergamon, Oxford
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Wamhoff H. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 5 (1984), Pergamon, Oxford 669-732
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Wamhoff, H.1
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15
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63749103162
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note
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2 (0 ppm) as internal standard.
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16
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63749087207
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note
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4, where L = 1-ethyl-5-nitro-1,2,3-triazole 8 (49 mg, 0.05 mmol). Decomposition temperature = 214 °C (10 °C/min, nitrogen atmosphere).
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17
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0034859107
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Abboud J.-L.M., Foces-Foces C., Notario R., Trifonov R.E., Volovodenko A.P., Ostrovskii V.A., Alkorta I., and Elguero J. Eur. J. Org. Chem. (2001) 3013-3024
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Ostrovskii, V.A.6
Alkorta, I.7
Elguero, J.8
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19
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63749126908
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note
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int = 0.0473). R1 = 0.0598 for 5368 reflections with I > 2σ(I), wR2 = 0.1775 for all data. CCDC reference number 703180.
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21
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0001405002
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0000648887
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4444303570
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16844363448
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