Methanol → 5-[1-(4-bromophenyl)-1-methylethyl]-1H-1,2,4-triazol-3-amine

Temperatur

0 °C

To a stirred mixture of N-aminoguanidine nitrate (2.1 g, 15 mmol) and anhydrous methanol (18 mL) cooled to 0° C. was added sodium methoxide solution (25% in methanol, 3.4 mL, 15 mmol) dropwise. The resulting mixture was stirred at 0° C. for 10 min before methyl 2-(4-bromophenyl)-2-methylpropanoate (1.0 g, 3.9 mmol) was added. The mixture was then stirred at 0° C. for 10 min, RT for 10 min, and 75 ° C. for 6 days. The reaction mixture was cooled and diluted with 20 mL of water. Methanol was removed under vacuum and the aqueous solution was acidified to pH=3-4 with 3 N aqueous HCl solution and extracted with ethyl acetate. The ethyl acetate layer was dried (Na2SO4) and concentrated. Silica gel flash chromatography purification gave 330 mg (31% yield) of the title compound as a yellow solid. (M+H)+=281.14

1. additionwas added
2. wait75 ° C. for 6 days
3. temperatureThe reaction mixture was cooled
4. customMethanol was removed under vacuum
5. extractionextracted with ethyl acetate
6. dry with materialThe ethyl acetate layer was dried (Na2SO4)
7. concentrationconcentrated
8. customSilica gel flash chromatography purification

ORD-Eintrag

ord-511b02996a9948c98880de54604fef60

Quelldatensatz

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07361654B2