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Chemical Structure| 1198416-32-8 Chemical Structure| 1198416-32-8

Structure of 1198416-32-8

Chemical Structure| 1198416-32-8

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Product Details of [ 1198416-32-8 ]

CAS No. :1198416-32-8
Formula : C14H11BrN2O2S
M.W : 351.22
SMILES Code : O=S(N1C(Br)=CC2=CC=CN=C21)(C3=CC=C(C)C=C3)=O
MDL No. :MFCD15529388
InChI Key :MDLNSMRCPJEEFR-UHFFFAOYSA-N
Pubchem ID :57374454

Safety of [ 1198416-32-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1198416-32-8 ]

* 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 [ 1198416-32-8 ]

[ 1198416-32-8 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1198416-32-8 ]
  • [ 1083181-25-2 ]
YieldReaction ConditionsOperation in experiment
80% With water; potassium hydroxide In methanolReflux A mixture of 209-3 (30 g, 0.085 mol), methanol (85OmL) and aqueous potassium hydroxide (5 mol/L, 100 mL) was heated under reflux overnight. The majority of the solvent was removed under vacuum, and the residue was partitioned between EtOAc and water. The organic layer was dried over anhydrous Na2SO4 and concentrated to give 209-4 (24 g, 80percent yield) which was used without further purification. 1H NMR (400 MHz, DMSO): 6.550 (s, 1H); 7.039 (dd, J=5.2 Hz, J=3.2 Hz, 1H); 7.857 (dd, J=1.6 Hz, J=3.2 Hz, 1H); 8.155 (q, J=1.6 Hz, 1H); 12.418 (br, 1H)
References: [1] Patent: US2009/318455, 2009, A1, . Location in patent: Page/Page column 98-99.
  • 2
  • [ 348640-02-8 ]
  • [ 1198416-32-8 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.33333 h;
Stage #2: With 1,2-dibromo-1,1,2,2-tetrachloroethane In tetrahydrofuran; hexane at -78 - 20℃;
A solution of 209-2 (50.0 g, 183.8 mmol) in dry THF cooled to -78° C. and n-BuLi (81 ml, 2.5 M in hexane) was added over 20 minutes. The resulted solution was maintained at -78° C. for 1 h, and then a solution of BrCl2CCCl2Br (71.0 g, 220.5 mmol) in dry THF was added. The mixture was stirred -78° C. for 30 min and allowed to warm slowly to room temperature. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic layer was dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography (5percent ethyl acetate in petroleum ether to 20percent ethyl acetate in petroleum ether as the eluent) to afford 209-3 (37 g, 58percent yield). MS-ESI: m/z=351.0 [M+1]+
References: [1] Patent: US2009/318455, 2009, A1, . Location in patent: Page/Page column 98-99.
 

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