Hydrochloric Acid → 3-(Methylthio)-5-phenyl-6-p-tolyl-1,2,4-triazine

To a suspension of 2-(hydroxyimino)-2-phenyl-1-p-tolylethanone (1.99 g, 8.32 mmol) in a 1:1 mixture of MeOH/H2O (40.0 mL) was added hydrazinecarbothioamide (1.134 g, 12.44 mmol) followed by concentrated HCl (0.75 mL, 24.68 mmol). The reaction was stirred at room temperature for 1 h then at 60° C. overnight. Additional hydrazinecarbothioamide (˜3×100 mg) was added portionwise and the reaction was stirred at 60° C. until the starting material was consumed. The reaction was neutralized with saturated NaHCO3. The solid was removed by filtration and rinsed with H2O. To the solid was added a solution of potassium carbonate (5.78 g, 41.8 mmol) in H2O (85 mL) and the mixture was heated at 90° C. overnight. The reaction mixture was cooled to room temperature then placed in an ice bath. Iodomethane (0.52 mL, 8.35 mmol) was added and the reaction was stirred at 0° C. and then slowly warmed to room temperature. After stirring overnight, the solution was decanted. The solid was dissolved in CH2Cl2, and the solution was washed with H2O and brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow solid (1.302 g). LCMS m/z=294.2 [M+H]+.

1. customat 60° C.
2. customovernight
3. stirringthe reaction was stirred at 60° C. until the starting material
4. customwas consumed
5. customThe solid was removed by filtration
6. washrinsed with H2O
7. temperaturethe mixture was heated at 90° C. overnight
8. temperatureThe reaction mixture was cooled to room temperature
9. customthen placed in an ice bath
10. stirringthe reaction was stirred at 0° C.
11. temperatureslowly warmed to room temperature
12. stirringAfter stirring overnight
13. customthe solution was decanted
14. dissolutionThe solid was dissolved in CH2Cl2
15. washthe solution was washed with H2O and brine
16. dry with materialdried over MgSO4
17. concentrationconcentrated
18. customThe residue was purified by silica gel column chromatography

ORD record

ord-1f6645aad51e44c2afcc8ea7311c1c99

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940891B2