Guanidine Hydrochloride → HCID 136068845, compound

Participants

Reaction Steps

Guanidine hydrochloride (4.18 g, 43.7 mmoles) was added to a solution of sodium ethoxide (65.6 mmoles) in ethanol (25 mL), and the mixture was treated with compound 1A (7.0 g, 21.9 mmoles) as a solution in ethanol (25 mL) and then refluxed for 7 hours. After cooling, the mixture was filtered, the solid residue was washed with 3 volumes (10 mL) of ethanol, and the combined filtrate and washings were treated with acetic acid to pH ~ 7.0. The filtrate was evaporated in vacuo to a viscous residue and treated with water (50 mL). Filtration gave a solid, which was washed with 3 volumes (10 mL) of water and dried at 50° C. in vacuo to give 6.76 g (93%) of compound 1B as a white solid. NMR (DMSO-d6) δ 1.28 (t, 3H, CH3 of ester), 1.75 (m, 2H, CH2 --CH2 -- CH2), 2.25 (t, 2H, CH2 --CH2CH2 --O), 3.97 (t, 2H, --CH2 --O), 4.25 (q, 2H, CH2 of ester), 5.7 (s, 2H, NH2), 5.93 (s, 2H, NH2), 6.98 (d, 2H, benzoate H's ortho to oxygen), 7.85 (d, 2H, benzoate H's ortho to carbonyl), 9.8 (br s, 1H, ring NH). The intermediate, compound 1B, was used in the next reaction without further purification.

Provenance & Evidence