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604-50-2

604-50-2 Structure

604-50-2 Structure
IdentificationBack Directory
[Name]

1-methylquinazoline-2,4(1H,3H)-dione
[CAS]

604-50-2
[Synonyms]

NSC401254
NSC 401254
Glycosmicine
1-methylquinazoline-2,4-dione
1-methylquinazoline-2,4-quinone
1-methylquinazoline-2,4(1H,3H)-dione
1-Methyl-2,4(1H,3H)-quinazolinedione
2,4(1H,3H)-QUINAZOLINEDIONE, 1-METHYL-
Methyl-1 (1H,3H)quinazolinedione-2,4 [French]
1-Methyl-1,2,3,4-tetrahydroquinazoline-2,4-dione
1-methyl-2,4(1H,3H)-quinazolinedione(SALTDATA: FREE)
1-Methyl-5,6-[1,3]butadienopyrimidine-2,4(1H,3H)-dione
[Molecular Formula]

C9H8N2O2
[MDL Number]

MFCD00731030
[MOL File]

604-50-2.mol
[Molecular Weight]

176.18
Chemical PropertiesBack Directory
[storage temp. ]

Inert atmosphere,Room Temperature
[Appearance]

White to off-white Solid
Spectrum DetailBack Directory
[Spectrum Detail]

1-methylquinazoline-2,4(1H,3H)-dione(604-50-2)1HNMR
Hazard InformationBack Directory
[Synthesis]

N-METHYLANTHRANILIC ACID

119-68-6

Sodium cyanate

917-61-3

1-methylquinazoline-2,4(1H,3H)-dione

604-50-2

An aqueous solution (25 mL) of sodium cyanate (28 mmol) was added dropwise to an aqueous solution (50 mL) of N-methyl-phthalaminobenzoic acid (20 mmol) and acetic acid (0.2 mL) under stirring conditions. When the temperature of the reaction mixture rose to 40 °C, sodium hydroxide was added in batches until the reaction temperature reached 75 °C. The reaction temperature was maintained at this temperature with continuous stirring for 4 hours. This temperature was maintained and the reaction was stirred continuously for 4 hours without cooling. Upon completion of the reaction, the precipitated crystals were collected by filtration and dissolved in boiling water (50 mL). Subsequently, the above solution was acidified with 50% sulfuric acid solution to pH 1-2. The precipitated crystals were filtered, washed with water and finally recrystallized from 50% acetic acid solution to afford the target product 1-methyl-2,4(1H,3H)-quinazolinedione (2.92 g, 84% yield); the melting point was 278 °C. The reaction was carried out at a temperature of 75 °C for 4 hours.

[References]

[1] Chemistry of Heterocyclic Compounds, 2009, vol. 45, # 12, p. 1508 - 1514
[2] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 110, p. 324 - 332
[3] Patent: WO2016/92326, 2016, A1. Location in patent: Page/Page column 97; 113
[4] Patent: EP3299371, 2018, A1. Location in patent: Paragraph 0525; 0526
[5] Letters in Drug Design and Discovery, 2014, vol. 11, # 6, p. 712 - 720
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