Hydrochloric Acid → 4,6-dichloro-N-(3-fluorophenyl)-1,3,5-triazin-2-amine

Participants

Reaction Conditions

Reaction Steps

To cyanuric chloride (1.6614 g, 9 mmol) dissolved in acetone (20 mL) stirring at 0-5° C., was added a solution of 3-fluoroaniline (0.9 mL, 9 mmol) in acetone (5 mL) followed by the addition of 2.5 N NaOH (3.6 mL, 9 mmol). The reaction mixture was allowed to stir at 0-5° C. for 1 hour under nitrogen. The reaction mixture was poured over crushed ice and neutralized with 10% HCl and 10% NaOH. The solid that formed was collected by vacuum filtration and the resulting solid was dried overnight under vacuum. Flash column chromatography (SiO2, 70:30 hexanes:ethyl acetate) yielded a faint yellow solid (159a, 1.67 g, 72%), mp 143° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 23.5 min, 87.0% purity.

Provenance & Evidence