3-[(4-methylphenyl)methylsulfanyl]-1H-1,2,4-triazol-5-amine synthesis
- Product Name:3-[(4-methylphenyl)methylsulfanyl]-1H-1,2,4-triazol-5-amine
- CAS Number:312275-49-3
- Molecular formula:C10H12N4S
- Molecular Weight:220.29
Yield:312275-49-3 66%
Reaction Conditions:
with sodium hydroxide in ethanol;water at 75; for 0.333333 h;
Steps:
5-((4-methylbenzyl)thio)-4H-1,2,4-triazol-3-amine (13)
In a 250-mL Erlenmeyer flask, 2.32 g (0.02 mol) of 3-amino-5-thio-1,2,4-triazole was mixed with 20 mL of1 M NaOH solution (0.04 mol). To this solution was added 3.75g (0.02 mol) of 1-(bromomethyl)-4-methylbenzene dissolved in 40 mL of absolute ethanol. The yellowish green mixture was refluxed in theoil bath at 75 °C for 20 min until the turbidity disappeared and the color of the solution turned to amber. The solution was evaporated under the reduced pressure to about 25 mL, diluted with 5 mL distilled water, and refrigerated overnight. The precipitate was filtered, mixed with toluene and was azeotroped with the toluene under the reduced pressure. The crude residue was recrystallized from hot chloroform to yield a white solid (2.93 g, 66%); mp: 109-110 oC; FT-IR (cm-1): 3439.64, 3329.11, 3226.21, 3063.36,2919.17, 2851.98, 1636.92, 1500.70, 1445.72, 1365.40; 1H NMR (300 MHz, DMSO-d6, ppm): 2.26(s, 3H),4.17 (s, 2H), 7.09 (d, J = 7.86 Hz, 2H), 7.23 (d, J = 8.01 Hz, 2H); 13C NMR (75 MHz, DMSO-d6, ppm): 21.1,35.1, 129.1, 129.3, 135.7, 136.6, 156.2, 157.8; MS (ESI): 220.9 (M-H)+; Anal. HPLC (Rt: 7.14 min; Height:529. 96; mAUArea%: 96%).
References:
Helgren, Travis R.;Chen, Congling;Wangtrakuldee, Phumvadee;Edwards, Thomas E.;Staker, Bart L.;Abendroth, Jan;Sankaran, Banumathi;Housley, Nicole A.;Myler, Peter J.;Audia, Jonathon P.;Horn, James R.;Hagen, Timothy J. [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 3,p. 813 - 824] Location in patent:supporting information
104-82-5
352 suppliers
$10.00/5mL
16691-43-3
362 suppliers
$15.00/5g
312275-49-3
6 suppliers
inquiry
