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Chemical Structure| 146137-93-1 Chemical Structure| 146137-93-1

Structure of 146137-93-1

Chemical Structure| 146137-93-1

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Product Details of [ 146137-93-1 ]

CAS No. :146137-93-1
Formula : C11H7NO2S
M.W : 217.24
SMILES Code : O=C(C1=CC2=CC(C#N)=CC=C2S1)OC
MDL No. :MFCD11044578

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Application In Synthesis of [ 146137-93-1 ]

* 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.

  • Downstream synthetic route of [ 146137-93-1 ]

[ 146137-93-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 2365-48-2 ]
  • [ 146137-79-3 ]
  • [ 146137-93-1 ]
YieldReaction ConditionsOperation in experiment
1.18 g With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h; A mixture of 1.00 g of 2-fluoro-5-cyanobenzaldehyde, 855 mg of methyl thioglycolate, 1.02 g of potassiumcarbonate, and 15 ml of N,N-dimethylformamide was stirred for 2 hours at 60°C. The reaction mixture was cooled toroom temperature. Water was added to the reaction mixture, and extraction was performed three times by using ethylacetate. The collected organic layer was with water and saturated saline, dried over magnesium sulfate, and thenconcentrated under reduced pressure, thereby obtaining 1.18 g of methyl 5-cyanobenzo[b]thiophene-2-carboxylate.
YieldReaction ConditionsOperation in experiment
64% Benzo[b]thiophene-5-carboxamidine hydrochloride 4-Fluorobenzonitrile was formylated with LDA and DMF in THF at -78° C. under the usual conditions to give 4-fluoro-3-formylbenzonitrile in 77percent yield. This was annulated under the usual conditions with NaH and methyl thioglycollate to give methyl 5-cyanobenzo[b]thiophene-2-carboxylate in 64percent yield.
  • 3
  • methylthioglycollate [ No CAS ]
  • [ 146137-79-3 ]
  • [ 146137-93-1 ]
YieldReaction ConditionsOperation in experiment
86.4% With potassium tert-butylate; In tetrahydrofuran; ice-water; chloroform; EXAMPLE 113 Methyl 5-cyano-benzthiophene-2-carboxylate Methylthioglycollate was added to t-BuOK (43 mL, 1M in THF) in a flame dried flask cooled in ice-water bath. An additional 100 mL of dry THF was added and the mixture was stirred at room temperature for 30 min. A solution of <strong>[146137-79-3]2-fluoro-5-cyano-benzaldehyde</strong> from Example 112 (6g, 0.04 mol) in 100 mL of dry THF was added dropwise via a syringe over a period of 30 min. The reaction was exothermic and a considerable darkening of the reaction mixture was observed. The reaction mixture was stirred for another 30 min. at room temperature. The mixture was carefully added to an ice-water mixture and the precipitated was removed by filtration. The precipitate was dissolved in chloroform and dried over magnesium sulfate. The solution was filtered and evaporated to give methyl 5-cyano-benzthiophene-2-carboxylate (7.5 g, 86.4percent yield). 1H NMR (CDCl3): d 8.16 (s, 1H), 8.04 (s, 1H), 7.92 (d, 1H, J=8.5 Hz), 7.62 (d, 1H, J=8.5 Hz).
 

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