9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one

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9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Basic information
Product Name:9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one
Synonyms:9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one;9-Bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one;[1,2,4]Triazolo[1,5-c]quinazolin-5(6H)-one,9-bromo-;9-bromo-[1,2,4]triazolo[4,3-c]quinazolin-5(6H)-one;Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one
CAS:882517-92-2
MF:C9H5BrN4O
MW:265.07
EINECS:
Product Categories:
Mol File:882517-92-2.mol
9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Structure
9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Chemical Properties
density 2.09
storage temp. Sealed in dry,Room Temperature
pka7.00±0.20(Predicted)
Safety Information
HS Code 2933599590
MSDS Information
9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Usage And Synthesis
Synthesis
Ethyl (4-bromo-2-cyanophenyl)carbamate

220269-80-7

Formylhydrazine

624-84-0

9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one

882517-92-2

General procedure for the synthesis of 9-bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one from (4-bromo-2-cyanophenyl)carbamic acid ethyl ester and formylhydrazine: to a solution of (4-bromo-2-cyanophenyl)carbamic acid ethyl ester (40.4 g, 150 mmol) in N-methyl pyrrolidone (NMP, 170 mL), was added formylhydrazine ( 10.0 g, 150 mmol). The reaction mixture was stirred at 160°C for 1.5 hours in a mild nitrogen atmosphere. Upon completion of the reaction, the mixture was cooled to below 100°C and water (340 mL) was slowly added. The resulting slurry was further cooled to 25°C and stirred continuously for 15 minutes. The precipitated solid was collected by filtration and washed sequentially with water and 2-propanol. Finally, the product was dried under vacuum to afford 9-bromo-[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one (32.4 g, 81% yield) as a light yellow solid. Mass spectrometry (MS) analysis result: m/e = 264.9/267.0 (M + H+).

References[1] Patent: US2006/84642, 2006, A1. Location in patent: Page/Page column 9
[2] Patent: US2006/84801, 2006, A1. Location in patent: Page/Page column 12
[3] Patent: US2006/79507, 2006, A1. Location in patent: Page/Page column 18
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 20, p. 5940 - 5944
9-Bromo-6H-[1,2,4]triazolo[1,5-c]quinazolin-5-one Preparation Products And Raw materials
Raw materialsEthyl (4-bromo-2-cyanophenyl)carbamate-->Formylhydrazine-->N-Methyl-2-pyrrolidone-->Water
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