Sodium ethoxide → HCID 178479326, compound

Participants

Reaction Steps

To sodium ethoxide [prepared by reacting sodium (60 mg, 2.61 mmol) and anhydrous ethanol (5 ml)] benzylguanidine hydrochloride (580 mg, 3.12 mmol) was added and refluxed in an oilbath for 1 hour. The reaction mixture was cooled to room temperature and insoluble materials filtered. Methyl 2,6-dichlorophenylacetate (285 mg, 1.3 mmol) (CH3(C═O)CH2(2,6,-di-ClC6H3) was added to the filtrate and refluxed for 2 hours. After cooling to room temperature the reaction mixture was concentrated and converted to the hydrochloride salt by the addition of hydrogen chloride (1M in ether) to provide 310 mg of N-(2,6-dichlorophenylacetyl)-N′-benzylguanidine hydrochloride as a white solid, purity 89.3% (HPLC); 1H-NMR (CD3OD) δ 4.38 (s, 4H, CH2), 7.32–7.41 (m, 8H, Ar).

Provenance & Evidence