Acetyl chloride → HCID 67106715, compound

Participants

Reaction Steps

4-(6-hydroxy-indan-1-ylmethyl)-1H-imidazol-1-ium chloride (100 mg, 0.399 mmol) was dissolved in 1 ml of trifluoroacetic acid (TFA) and acetic acid chloride (0.510 mmol) was added. The mixture was stirred at room temperature for 24 h. TFA was evaporated and the residue was dissolved in water and made basic with 2 M NH3 (aq.). The aqueous phase was extracted with dichloromethane (DCM). The combined extracts were dried (Na2SO4) and evaporated. The residue was dissolved in diethyl ether and the solution was saturated with dry HCl gas. The precipitate was filtered and dried under vacuum. Yield 105 mg (82%) of a white hygroscopic solid. 1H NMR (CDCl3, TMS): δ 1.72 (m, 1H), 2.18-2.26 (m, 4H), 2.72-2.87 (m, 3H), 3.17 (dd, 1H), 3.56 (qui, 1H), 6.85 (m, 2H), 6.92 (s, 1H), 7.16 (d, 1H), 8.61 (s, 1H), 14.44 (s, 2H). 13C NMR (CDCl3, TMS): δ 21.11, 29.60, 30.46, 31.68, 43.93, 115.72, 117.00, 120.29, 125.33, 132.32, 132.40, 141.37, 146.32, 149.39, 170.11. HPLC-MS (EI): m/z=257.2 ((M+H)+—Cl−. Anal.—Calc. for C15H16N2O2.HCl.0.2CH2Cl2: C, 58.94; H, 5.66; N, 9.04. Found C, 58.66; H, 5.78; N, 8.83.

Provenance & Evidence