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ChemicalBook--->CAS DataBase List--->550-28-7

550-28-7

550-28-7 Structure

550-28-7 Structure
IdentificationBack Directory
[Name]

amisometradine
[CAS]

550-28-7
[Synonyms]

Rolicton
amisometradine
Aminoisometradin
Aminoisometradine
6-Amino-3-methyl-1-(2-methylallyl)uracil
6-amino-3-methyl-1-(2-methylallyl)pyrimidine-2,4-quinone
6-amino-3-methyl-1-(2-methylprop-2-enyl)pyrimidine-2,4-dione
6-azanyl-3-methyl-1-(2-methylprop-2-enyl)pyrimidine-2,4-dione
6-Amino-3-methyl-1-(2-methyl-2-propenyl)pyrimidine-2,4(1H,3H)-dione
2,4(1H,3H)-Pyrimidinedione, 6-amino-3-methyl-1-(2-methyl-2-propen-1-yl)-
[EINECS(EC#)]

208-980-3
[Molecular Formula]

C9H13N3O2
[MDL Number]

MFCD00867343
[MOL File]

550-28-7.mol
[Molecular Weight]

195.22
Chemical PropertiesBack Directory
[Melting point ]

175°
[Boiling point ]

331.89°C (rough estimate)
[density ]

1.1985 (rough estimate)
[refractive index ]

1.5100 (estimate)
[storage temp. ]

Amber Vial, -20°C Freezer, Under inert atmosphere
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

4.97±0.70(Predicted)
[color ]

White to Pale Beige
[Stability:]

Light Sensitive
Hazard InformationBack Directory
[Originator]

Rolicton,Searle,US,1956
[Uses]

Amisometradine is an oral diuretic.
[Definition]

ChEBI: Amisometradine is a pyrimidone.
[Manufacturing Process]

Preparation of the ethyl analog is as follows (methyl isocyanate is used in amisometradine manufacture).
To a cooled and stirred solution of 142 parts of methallylamine in 900 parts of benzene, 156 parts of ethyl isocyanate are added dropwise. Upon concentration in vacuum N-ethyl-N'-methallylurea is obtained.
260 parts of this urea derivative are dissolved in 500 parts of acetic anhydride and treated with 157 parts of cyanoacetic acid at 60°C and heated at that temperature for 2 hours. The solution is then concentrated in vacuum to a syrup. 100 parts of water are added and the vacuum distillation is repeated. The remaining syrup contains a mixture of N-cyanoacetyl-N-ethyl-N'- methallylurea and a small quantity of N-cyanoacetyl-N-methallyl-N'-ethylurea.
This syrup is treated with sufficient 20% sodium hydroxide solution to raise the pH to 10. A violent reaction occurs. The reaction mixture is diluted with 50 parts of water, stirred, cooled and filtered. The material collected on the filter is recrystallized from 10% ethanol to yield a mixture of 1-methallyl-3-ethyl-6- amino-1,2,3,4-tetrahydro-2,4-pyrimidinedione and 1-ethyl-3-methallyl-6- amino-1,2,3,4-tetrahydro-2,4-pyrimidinedione melting at about 157-159°C.
[Therapeutic Function]

Diuretic
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