Sodium Hydroxide → 5-(Trifluoromethyl)-1,2,4-triazin-3-amine

To a stirred solution of sodium acetate trihydrate (22.62 g, 166.2 mmol) in water (80 ml) was added 1,1-dibromo-3,3,3-trifluoroacetone (21.57 g, 79.9 mmol). The solution was heated at reflux under nitrogen for 30 min, then allowed to cool to room temperature before adding solid aminoguanidine bicarbonate (10.88 g, 79.9 mmol). The resulting pale yellow solution (pH 5) was stirred at room temperature for 3 h, then 4 N aqueous NaOH solution (40 ml, 160 mmol) was added causing a precipitate to appear. The mixture (pH 10) was stirred under nitrogen for a further 39 h. The solid was collected by filtration, washed with water and dried at 60° C. under vacuum to give 6.96 g of a mixture of two isomers in a 28:72 ratio. This was further purified by flash chromatography (silica gel, 30% EtOAc/isohexane), then recrystallised from ethanol to afford 3.53 g (27%) of the title compound: 1H NMR (400 MHz, DMSO-d6) δ8.00 (2H, br s), 9.08 (1H, s).

1. temperatureThe solution was heated
2. temperatureat reflux under nitrogen for 30 min
3. filtrationThe solid was collected by filtration
4. washwashed with water
5. customdried at 60° C. under vacuum

ORD record

ord-9a2a0d0af86942a39d98e3abf3b0c2aa

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696444B2