Réaction #2286313

Équation de réaction

2-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid

mercaptoacetic acid

→

[1,2,4]triazine-3,5-dione

Rendement 40.0%

2-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-[1,2,4]triazine-3,5-dione

Rendement 40.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was then cooled to room temperature
2. 2
   Extractionextracted with ethyl acetate (25 mL)
3. 3
   AutreThe organic layer was separated
4. 4
   Lavagewashed with a 1N aqueous sodium hydroxide solution (3×10 mL)
5. 5
   FiltrationThe resulting solids were filtered
6. 6
   Lavagerinsed well with water
7. 7
   AutreThe solids were dried under vacuum

Mode opératoire

2-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (49) (101.5 mg, 0.224 mmol) was treated with mercaptoacetic acid (2.2 mL). The reaction mixture was stirred with a magnetic stirrer and was heated to 155° C. for 24 h. The reaction mixture was then cooled to room temperature, diluted with water (25 mL) and extracted with ethyl acetate (25 mL). The organic layer was separated and washed with a 1N aqueous sodium hydroxide solution (3×10 mL). The aqueous layers were combined and acidified to pH=4. The resulting solids were filtered and rinsed well with water followed by petroleum ether. The solids were dried under vacuum to afford dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-[1,2,4]triazine-3,5-dione (50) (36 mg, 40%) as a tan solid; EI(+)-HRMS m/z calcd for C17H15Cl2N5O3 (M+H)1+ 408.0625, found 408.0626. Molecular Weight=408.2468; Exact Mass=407.0552

Source