Ethyl orthoformate → 1-((4-methoxyphenyl)methyl)-1H-1,2,3,4-tetrazole

Temperature

80 °C

A mixture of 3.84 g (28.0 mmol) of (4-methoxy)benzylamine, 2.73 g (42.0 mmol) of sodium azide and 7.50 mL (45.0 mmol) triethyl orthoformate in 25 mL of HOAc was stirred at 80° C. for 20 h. The reaction was cooled and concentrated. The residue was partitioned between 100 mL of EtOAc and 100 mL of H2O and the layers were separated. The organic layer was washed with 100 mL of 2.0 N HCl, 100 mL of sat'd NaHCO3, 100 mL of sat'd NaCl, dried over MgSO4 and concentrated. Flash chromatography on 100 g of silica gel using 2:1 v/v hexanes/EtOAc, then 1:1 v/v hexanes/EtOAc as the eluant afforded 2.32 g of the title compound: 1H NMR (300 MHz) δ 3.82 (s, 3H), 5.53 (s, 2H), 6.93 (d, J=8.6, 2H), 7.27 (d, J=8.6, 2H), 8.46 (s, 1H).

1. temperatureThe reaction was cooled
2. concentrationconcentrated
3. customThe residue was partitioned between 100 mL of EtOAc and 100 mL of H2O
4. customthe layers were separated
5. washThe organic layer was washed with 100 mL of 2.0 N HCl, 100 mL of sat'd NaHCO3, 100 mL of sat'd NaCl
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-4f3df1f3124e413c9b4bc171c0423abb

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265434B1