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Chemical Structure| 321913-54-6 Chemical Structure| 321913-54-6

Structure of 321913-54-6

Chemical Structure| 321913-54-6

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Product Details of [ 321913-54-6 ]

CAS No. :321913-54-6
Formula : C16H14N2OS
M.W : 282.36
SMILES Code : N#CC(C1=CC=C(SC)C=C1)C(C2=CC=C(C)N=C2)=O

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Application In Synthesis of [ 321913-54-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 321913-54-6 ]
  • Downstream synthetic route of [ 321913-54-6 ]

[ 321913-54-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 321913-54-6 ]
  • [ 221615-72-1 ]
YieldReaction ConditionsOperation in experiment
5.2 g With hydrogenchloride In water; acetic acid; toluene at 20℃; Example-6 Preparation of 1-(6-methyl-3-pyridinyl)-2-[(4-Methylthio)phenyl]ethanone (V) [0068] To compound ( VI) (10 gm) (as per process described above in Example-4) was added a mixture of concentrate hydrochloric acid (75 ml) and Glacial acetic acid (25 ml) After completion of reaction it was cooled to room temperature and extracted with (12 ml) Toluene. [0069] The above reaction mass was added in to a mixture of (31.75 ml) ammonia solution and water (10.00 ml) and stirred. Reaction mass was adjusted to pH between 6.9 to 7.1 using sodium carbonate solution (5percent w/v) at 0-5° C. temperature. It was stirred for 60 minutes and filtered to obtain wet cake. Wet product was washed twice with (10 ml) water. Product wet cake was dissolved in (70 ml) dichloromethane followed by addition of (20 ml) water, stirred for 10 minutes and layers were separated. Aqueous layer was extracted twice with dichloromethane. Combined organic layer containing the product was washed with water (10.00 ml), dried over anhydrous sodium sulphate and purified by activated carbon treatment. [0070] Product layer was concentrated by distilling out dichloromethane at atmospheric pressure to obtain a semi-solid residue. The residue mass was degassed under vacuum for 30 minutes. Isopropyl alcohol (7.5 ml) was added to the mass and it was cooled to 8-10° C. temperature. After stirring for 1 hour at 8-10° C. temperature, it was filtered, and washed with chilled isopropyl alcohol (2.00 ml). The product was dried in a vacuum oven at 45°-50° C. to give dried product (7 gm, purity by HPLC 93.24percent) [0071] Dried product obtained (7 gm) was purified by treatment with methyl iso butyl ketone (17.5 ml). The product slurry was stirred for 30 minutes, filtered and washed with methyl iso butyl ketone (2 ml), and dried under vacuum oven at 40-45° C. temperature. The purified product (5.2 gm) showed HPLC purity 95.40percent.
References: [1] Patent: WO2012/66570, 2012, A2, . Location in patent: Page/Page column 13.
[2] Patent: US2013/245272, 2013, A1, . Location in patent: Paragraph 0068; 0069; 0070; 0071.
 

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