Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia UniversityChen, Yü-Gwan
Science
Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia University
Chen, Yü-Gwan
Organic compounds -- Synthesis; Selenium; Thesis (Ph. D.)
Five grams of the monoamino compound were mixed with powdered KOH,
heated together until the mixture just melted, and maintained in that
state for a few minutes. When the latter had cooled down to room
temperature, cold water was poured over the mixture. The filtered
solution was acidified until no further precipitate was formed. The
precipitate was collected and recrystallized from water, m.p. 121°C.
One gram of this solid was placed in a test tube, provided with a cork
and a delivery tube, and heated with soda lime; a liquid with the smell
of benzene was collected in another test tube cooled with water. When
this liquid was treated with a few drops of nitric acid mixture the
smell of nitrobenzene was given off. A gram of the crystals was heated
with concentrated sulphuric acid and alcohol when the odor of ethyl
benzoate was noted.
Monacetyl Derivative
Five grams of the monoamino selenazole were heated on a water-bath with
10 cc. of acetic anhydride until the solution was clear, which took
about two hours. 100 cc. of water were poured into the mixture, which
was then neutralized with dilute ammonium hydroxide. The precipitate
was filtered, decolorized by animal charcoal, and recrystallized from
dilute alcohol.
The acetyl compound, 6-acetamino-2-phenylbenzoselenazole, forms
colorless crystals, melting at 188.1°-.7°C. (corr.). It is insoluble in
ether, benzene, carbon disulphide; slightly soluble in toluene; soluble
in alcohol, ethyl acetate, amyl acetate, acetone, and acetic acid. A
pure sample was analyzed and gave the following result,
Calculated for
C₁₅H₁₂N₂SeO Found
Nitrogen 8.88% 8.92% 8.68%
Monobenzylidene Derivative
Five grams of the monoamino compound were dissolved in 200 cc. absolute
alcohol with the addition of 3 cc. of benzaldehyde and the clear
solution was boiled on a water-bath, with a return condenser, for two
hours. After the solution was boneblacked, the yellow precipitate was
recrystallized from carbon disulphide. The yield was 90 per cent.
It crystallizes in yellow plates, melting at 156.7°-157.6°C., soluble
in benzene, ether, ethyl alcohol, carbontetrachloride, acetone, but
difficultly soluble in ligroin. An analysis of the crystals showed the
following result,
Calculated for
C₂₀H₁₄N₂Se Found
Nitrogen 7.75% 7.92% 7.68%
An Azo Dye
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