Hydrochloric Acid → HCID 178424372, compound

Participants

Reaction Steps

N-(2-Methylphenyl)-N'-(2-methyl-4-aminophenyl)guanidine dihydrochloride (112 mg, 0.341 mmol) were dissolved in 2 ml H2O and 100 ul conc. HCl (1.2 mmol). The solution was cooled in an ice bath, and a solution of NaNO2 (42 mg, 0.61 mmol) in 450 ul H2O were added. The reaction mixture turned yellow, and was stirred for 45 min before solid NaN3 (43 mg, 0.661 mmol) was added in a single portion. After N2 evolution was caused, a foamy solid (11 mg) was removed and discarded. Solid NaOH (96 mg, 2.41 mmol) was added, and the bright yellow precipitate was extracted with Et2O (3×5 ml). Evaporation of the combined Et2O layers gave a yellow solid which was crystallized from EtOH/H2O: NMR (CD3OD) 2.279 (s, 3H), 2.284 (s, 3H), 6.864 (dd, 1H, J=2.4 Hz, 8.4 Hz), 6.914 (d, 1H, J=2.1 Hz), 7.055 (td, 1H, J=1.8 Hz, 7.2 Hz), 7.136-7.229 (m, 4H).

Provenance & Evidence