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.)
The diacetyl and dibenzylidene compounds were also prepared from these
diamino derivatives. The former crystallizes in cubes from dilute
alcohol; m. p., 307°C (Corr.) and the latter in beautiful yellow plates
from carbon disulphide, m. p., 195°-196°C. (Corr.). An analysis of
these two compounds showed the following results,
Calc. for Calc. for Found
C₁₇H₁₅N₃O₂Se C₂₇H₁₉N₃Se I II
Nitrogen 9.05% 11.21% 9.21% 11.43%
Dyeing with Azo Dyes
Both the monoamino and the diamino derivatives form intensely colored
dyes when diazotized and coupled with phenols and aromatic amines. The
dyes formed are fast to light. In the following table silk is given to
represent the fabrics used. Wool and cotton were dyed similar shades,
though with slight variation. Each silk sample was dyed in acid or
alkaline baths as indicated and each bath contained 0.01 gram in twenty
cc. solution:
Diazo. On Diazo. On
Coupler monoamine silk diamine silk
Phenol deep red v. light (alk) yellow
(alk) yellow deep red
Dimethylaniline orange light orange-red yellow
(acid) yellow (acid)
P-nitraniline light brownish grayish
brown (acid) brown
(acid)
P-toluidine light brownish brownish
brown (acid)
(acid)
Pyrogallic dark grayish dark grayish
acid brown brown
(acid) (alk)
Salicylic reddish light red brown
acid (alk) brown (alk)
B-naphthol deep red pink deep red red
(alk) (alk)
Sulphanilic light brownish brown brown
acid brown (alk)
(alk)
A-naphthylamine light brownish yellow yellow
brown (acid)
(acid)
Resorcinol purple red dark deep red
(alk) purple
(alk)
BIBLIOGRAPHY
1. Berzelius, Annales de Physique et Chimie (2) 9, 239, 356 (1818).
2. Gmelin-Kraut, “Handbuch der Anorg. Chemie” I (1) 705-804; Roscoe
and Schorlemmer, “Treatise on Chemistry” I, 467-82 (1920);
Browning, “Introduction to the Rarer Elements,” 144-52 (1917).
3. Victor Lenher, J. Ind. Eng. Chem., 12, 597 (1920).
4. Le Seleneum et ses applications actuelles, Chimie et Industrie
(1919) 245.
5. C. R. Boggs, U. S. A., 1,249,272; J. Ind. Eng. Chem. 10, 117-8
(1918).
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