Hydrochloric Acid → HCID 178419031, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-benzyloxy-phenylamine (20.0 g, 100.35 mmol) in 150 ml 1,4-dioxane in a 500 ml round bottom flask was added cyanamide (7.39 g, 175.95 mmol) followed by HCl in 1,4-dioxane (4M, 44 ml, 176.00 mmol). The resulting suspension was stirred and heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature then NaOH (6N, 35 ml, 210.00 mmol) was added. The volume of solution was reduced to 50 ml, in vacuo, and the resulting precipitate was collected by filtration. The solid product was dried in vacuo overnight to afford the aryl guanidine 9 (23.8 g) in 98.4% yield. 1H NMR (MeOH-d4) δ 6.4-7.5 (m, 9H), 5.1 (s, 2H).

Provenance & Evidence