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Benzonitrile, 4-(1H-1,2,4-triazol-5-yl)- synthesis

2synthesis methods
-

Yield:118863-78-8 48%

Reaction Conditions:

Stage #1: 4-cyanobenzamide;N,N-dimethyl-formamide dimethyl acetal for 8 h;Reflux;Inert atmosphere;
Stage #2: with hydrazine hydrate;acetic acid for 1 h;Reflux;

Steps:

15.1

Step 1. 4-(lH-[l,2,4]Triazol-3-yl)-benzonitrile. The general procedure outlined by Lin et. al. (J. Org. Chem. 1979, 44, 4163) for preparation of 3-(4-nitrophenyl)-lH- [l,2,4]triazole was used. 4-Cyanobenzamide (21.63 g, 0.148 mol) was dissolved in DMF- DMA (100 rnL) and was stirred at reflux under N2 for 8 h. The mixture was concentrated to dryness and suspended in AcOH (50 rnL). The vessel was then charged with hydrazine monohydrate (7.18 mL, 0.148 mmol) and stirred at reflux for 1 h before concentration. The desired 4-(lH-[l,2,4]triazol-3-yl)-benzonitrile was obtained in 98% purity by trituration with Et2O followed by filtration (12.17 g, 0.072 mol, 48%).

References:

WO2011/17513,2011,A1 Location in patent:Page/Page column 27-28