Sodium Azide → HCID 14153831, compound

Participants

Reaction Steps

A mixture of the chloromethyl ketone (7, 5.9 g, 0.022 mol), 10.8 g (0.16 mol) of NaN3 and 180 ml of 80% MeOH was stirred at room temperature for 20 hours. After evaporation of MeOH the aqueous residue was diluted to 100 ml with H2O and extracted with three 50 ml portions of CHCl3. The CHCl3 was dried (MgSO4) and evaporated to leave 5.5 g (91%) of a yellow oil (8); TLC (silica gel, CHCl3 0C6H6, 1:1) Rf 0.30 single spot; IR cm-1 2105 (--N3); NMR (CDCl3) δ 0.80 (3H, t, CH3), 1.70 (2H, m, CH2CH3), 2.80 (2H, m, CH2C=O), 3.15 (1H, m, Ar--CH), 3.77 (2H, s, CH2N3), 3.90 (3H, s, OCH3), 7.30 (2H, d, 3', 5'--ArH), 8.05 (2H, d, 2', 6'--ArH).

Provenance & Evidence