24047-25-4

Benezrial,Houde,France,1978

Antihypertensive.

ChEBI: Guanoxabenz is a dichlorobenzene.

2N sodium hydroxide solution (5 ml) is added to a stirred suspension of Smethylisothiosemicarbazide hydroiodide (2.33 g) and hydroxylamine hydrochloride (0.70 g) in water (6 ml) and stirred for 48 hours. The solution is evaporated in vacuo to provide 1-amino-3-hydroxyguanidine. One-third of the residue is dissolved in 16 ml of ethanol and 2,6-dichlorobenzaldehyde (0.6 g) is added to this solution. The reaction mixture is then stirred for 48 hours. The solution is then evaporated in vacuo and the residue dissolved in ether (30 ml) and in hydrochloric acid (30 ml). The aqueous phase is rendered alkaline with 2N sodium carbonate solution and extracted with ether. The ether layer is dried with sodium sulfate and evaporated. The residue is dissolved in ether and excess dry hydrogen chloride is passed into the solution.
The resultant mixture is evaporated in vacuo and the residue triturated with methylene chloride to afford a crude product. Recrystallization from ethanolether (1:3) provides 1-(2,6-dichlorobenzylideneamino)-3-hydroxyguanidine hydrochloride; MP 173°C to 175°C. When the above process is carried out and S-benzylisothiosemicarbazide hydroiodide is used in place of S-methylisothiosemicarbazide hydroiodide, the identical product is again obtained.

Antihypertensive