10.1002/ejoc.201601425
European Journal of Organic Chemistry
FULL PAPER
In a 100-mL two necked round bottom flask, compound 13 (10.0
mmol) is dissolved in DMSO (15 mL). The reaction mass is cooled to
5 to 10°C. At this temperature, aqueous KOH solution (20.0 mmol of
KOH is dissolved in 5 mL of water) is added slowly and stirred at 5 to
10°C for 15 min. Then, 1, 2-dibromoethane (1v) (10.0 mmol) is taken
in 10 mL of DMSO and is added slowly at 5 to 10°C and the reaction
mass is stirred at the same temperature for 10 min. The reaction
progress is monitored by TLC. After completion of the reaction, the
reaction mixture is quenched in crushed ice and then the product
(15) is extracted with diethyl ether (2x15 mL) twice. The solvent is
then evaporated under reduced pressure. The obtained crude
product (15) is purified by column chromatography using silica gel
(99:1 ratio of n-hexane and ethyl acetate).
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General experimental procedure for gram scale (25g scale)
synthesis:
A
mixture of 4-bromo phenacyl bromide (1k) (9.0 mol), 2-
mercaptobenzothiazole (2a) (9.0 mol) and ZnO (10.0% w/w) is taken
in a large porcelain bowl and ground together with a pestle for 5 min
at 25-30oC. After completion of the reaction, the crude mass is
washed with water (2x50 mL) twice and extracted with ethyl acetate
(2x25 mL) twice. Then the catalyst is separated by filtration under
vacuum. The organic layer is washed with water, dried with
anhydrous MgSO4 and the solvent is evaporated under reduced
pressure. The obtained product (3k) is purified by recrystallization
using ethanol.
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Acknowledgements
The authors acknowledge the financial support for this work
Council of Scientific and Industrial Research (CSIR), New Delhi,
Government of India under a major research project (No.
01(2391)/10/EMR-II) and University Grants Commission (UGC)
for providing UGC-SRF Fellowship to Mr. P. Md. Khaja
Mohinuddin.
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K.- Zamola, Heterocycles 2001, 55, 2085-2098. (b) C. Angelini,
Ann. Chim. 1955, 45, 162-165.
Keywords: Mechanochemical synthesis, C-S bond construction,
Phenacyl/benzyl/alkyl bromides, Thiols, ZnO.
Supporting information available: Physical and spectral (1H
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Metal Chemistry 2002, 25, pp. 291-296; (b) C. G. Densmore, H.
Wheeler, R. Cohenour, T. W. Robison, D. Hasam, B. J.
Cordova, P. C. Stark, E. N. Fuller, C. J. Cook, H. A. Weber,
Org. Process Res. Dev. 2007, 11, 996-1003.
and 13C NMR and HRMS) data of the synthesized compounds. See
doi:
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