ChemicalBook CAS DataBase List 1-(4-Nitrophenyl)methyl-1,2,4-triazole

1-(4-Nitrophenyl)methyl-1,2,4-triazole synthesis

8synthesis methods

Product Name:1-(4-Nitrophenyl)methyl-1,2,4-triazole
CAS Number:119192-09-5
Molecular formula:C9H8N4O2
Molecular Weight:204.19

584-13-4
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$5.00/5g

7440-44-0 Synthesis

7440-44-0
301 suppliers
$12.00/25g

100-11-8
9 suppliers
$13.00/5g

119192-09-5
104 suppliers
$80.00/1 g

Yield: 83.3%

Reaction Conditions:

with hydrogenchloride;sodium nitrite in water;isopropyl alcohol

Steps:

2.i Step (i):
Step (i): "One-pot" preparation of 1-(4-nitrobenzyl)-1,2,4-triazole (V; E=CH₂) 4-Nitrobenzyl bromide (64.22 g), 4-amino-1,2,4-triazole (26 g) and isopropyl alcohol (586 ml) were stirred together at reflux for 71/2 hours. The isopropanol solvent was replaced with water by using an azeotropic distillation procedure, in vacuo, on a Buchi rotary evaporator. The volume of the final aqueous slurry was 750 ml. 675 ml of this slurry was cooled to -2° C. and hydrochloric acid (50.8 ml, 12 M) added over a few minutes. A solution of sodium nitrite (21.7 g) in water (86 ml) was then added dropwise, and subsurface over a 40 minute period. The temperature of the batch was kept between -2° and -1° C. during the addition and then allowed to warm to 18° C. over 30 minutes. The temperature was then increased to 28° C. and held for 1 hour and the solution treated with charcoal (4.5 g, Fisons) for 15 minutes. The charcoal was removed and the filtrate (750 ml) divided equally in two. One half of the solution was made basic with ammonia solution (22 ml) and the precipitated base collected, washed with water (2*30 ml) and dried (16 hours at 35° C. in vacuo). This gave an 83.3% yield (22.73 g) of 1-(4-nitrobenzyl)-1,2,4-triazole.

References:

Merck, Sharp & Dohme, Ltd. US5567819, 1996, A

288-88-0 Synthesis