1-(diethoxymethyl)-1H-imidazole → HCID 14978579, compound

Participants

Reaction Conditions

Reaction Steps

The 2-lithio salt solution of 1-diethoxymethylimidazole was added dropwise (15 min) into a cooled (-78° C.) THF solution (130 mL) of 2-acetamido-N-benzyl-2-bromoacetamide (prepared from 2-acetamido-N-benzyl-2-ethoxyacetamide (2.00 g, 8.0 mmol) and BBr3 (1M in CH2Cl2, 10 mL, 10.0 mmol)). The reaction was stirred at -78° C. (1 h) and then quenched with a saturated aqueous NH4Cl (50 mL) solution. The mixture was stirred at room temperature (30 min), and made basic ("pH" 9.2)by adding aqueous K2CO3. The aqueous mixture was extracted with EtOAc (3×100 mL), and the combined extracts were dried (Na2SO4). The solvents were removed in vacuo and the residue was purified by flash column chromatography on SiO2 gel (2.5% MeOH/CHCl3) to give 0.14 g (7%) of the desired product: mp 228°-230° C. (recrystallized from EtOH); Rf 0.46 (10% MeOH/CHCl3); IR (KBr) 3200 (br), 1610, 1500 (br), 1430, 1350, 740, 680 cm-1 ; 1H NMR (DMSO-d6) δ 1.91 (s, C(O)CH3), 4.29 (d, J=5.6 Hz, CH2), 5.51 (d, J=7.7 Hz, CH), 6.85 (br s, C4H), 7.05 (br s, C5H), 7.18-7.30 (m, 5 PhH), 8.42 (d, J=7.7 Hz, NH), 8.65 (t, J=5.6 Hz, NH), 11.91 (br s, NH); 13C NMR (DMSO-d6) 22.49 (C(O)CH3), 42.21 (CH2), 51.62 (CH), 126.60 (C4'), 126.98 (2C2' or 2C3'), 127.21 (C4), 128.09 (2C2' or 2C3'), 128.32 (C5), 139.05 (C1'), 143.74 (C2), 168.12 (C(O)NH), 169.30 (C(O)CH3) ppm; mass spectrum (FD) 273 (M+ +1, 65), 272 (M+, 100).

Provenance & Evidence