Ethyl bromoacetate → HCID 57861289, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-aminotetrazole (10.0 g, 0.12 mol), ethyl bromoacetate (20.0 g, 0.12 mol), and Cs2CO3 (40.0 g, 0.13 mol) in acetonitrile (220 mL) is stirred and refluxed for 5 hours. The mixture is cooled to 50° C. and filtrated. The resulting filtrate is concentrated to give the crude coupling product. The mixture of the crude product and 3,5-bis(trifluoromethyl)benzaldehyde (25.0 g, 0.10 mol) in toluene (220 mL) is stirred and refluxed for 5 hours. After cooling to room temperature, the resulting mixture is concentrated. NaBH4 (4.4 g, 0.12 mol) is added portionwise slowly to EtOH (220 mL) solution of the resulting residue, and the mixture is stirred at room temperature for 2 days. After addition of sat. NH4Cl aq. and water, the mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give 2-(5-{N-[3,5-bis(trifluoromethyl)benzyl]amino}tetrazol-2-yl)ethanol.

Provenance & Evidence