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2165-19-7

2165-19-7 Structure

2165-19-7 Structure
IdentificationBack Directory
[Name]

Guanoxan
[CAS]

2165-19-7
[Synonyms]

Guanoxan
Guanoxane
Guanoxan USP/EP/BP
2-(GuanidinoMethyl)-1,4-benzodioxan
(1,4-Benzodioxan-2-ylmethyl)guanidine
1-(2,3-Dihydro-1,4-benzodioxin-2-ylmethyl)guanidine
2-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)guanidine
N-[(2,3-Dihydro-1,4-benzodioxin-2-yl)Methyl]guanidine
Guanidine, N-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-
[Molecular Formula]

C10H13N3O2
[MOL File]

2165-19-7.mol
[Molecular Weight]

207.23
Chemical PropertiesBack Directory
[Melting point ]

164-165°
[Boiling point ]

339.3±45.0 °C(Predicted)
[density ]

1.40±0.1 g/cm3(Predicted)
[pka]

pKa 12.3 (Uncertain)
Hazard InformationBack Directory
[Chemical Properties]

Guanidine sulfate (5714-04-5) is a white crystalline powder with a melting point of 205-208°C. It is soluble in water and has an odorless, bitter taste.
[Originator]

Envacar,Pfizer
[Uses]

Guanoxan is a sympatholytic drug related to Guanethidine (G815000). Guanoxan is used in the treatment of hypertension.
[Definition]

ChEBI: Guanoxan is a benzodioxine.
[Manufacturing Process]

2 Methods of producing of 2-guanidinemethyl-2,3-dihydro-1,4-benzodioxine:
1. 3.3 parts by weight of 2-aminomethyl-1,4-benzodioxane and 2.78 parts by weight of S-methylisothiouronium sulfate were dissolved in 20 parts by volume of water, and the resulting aqueous solution was heated under reflux for 3 h. At the end of this time, the solvent was removed by means of evaporation under reduced pressure and the residue so obtained dissolved in a minimum amount of fresh water and treated with charcoal. Upon filtration, there was obtained a clear filtrate which, on standing, soon afforded pure crystals of di(2-guanidinomethyl-1,4-benzodioxane)sulfate, melting point 204°-205°C.
The base 2-guanidinemethyl-2,3-dihydro-1,4-benzodioxine may be obtained by reaction of di(2-guanidinomethyl-1,4-benzodioxane)sulfate with, for example, sodium hydroxide.
2. o-Dihydroxybenzene reacted with epichlorhydrine in the presence sodium hydroxide and 2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine was obtained. To solution of 2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine thionylchloride was added to give 2-chlormethyl-2,3-dihydro-1,4-benzodioxine.
2-Chloromethyl-2,3-dihydro-1,4-benzodioxine reacted with benzylamine to produced 2-benzylaminomethyl-2,3-dihydro-1,4-benzodioxine, which was reduced at the presence of hydrogen and Pd-C (catalyst) to 2-aminomethyl- 2,3-dihydro-1,4-benzodioxine.
2-Aminomethyl-2,3-dihydro-1,4-benzodioxine was treated by Smethylisothiouronium sulfate and there was produced 2-guanidinemethyl-2,3- dihydro-1,4-benzodioxine.
[Brand name]

Envacar (Pfizer).
[Therapeutic Function]

Antihypertensive
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