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Chemical Structure| 5919-29-9 Chemical Structure| 5919-29-9

Structure of 5919-29-9

Chemical Structure| 5919-29-9

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Product Details of [ 5919-29-9 ]

CAS No. :5919-29-9
Formula : C13H17NO3S
M.W : 267.34
SMILES Code : O=C(C1=C(NC(C)=O)SC2=C1CCCC2)OCC
MDL No. :MFCD00087275

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Application In Synthesis of [ 5919-29-9 ]

* 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 [ 5919-29-9 ]

[ 5919-29-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 5919-29-9 ]
  • [ 7311-95-7 ]
YieldReaction ConditionsOperation in experiment
34% With disulfur; phthalic acid dimethyl ester; at 195℃; for 8.0h; Step 3; Preparation of ethyl 2-amino-l-benzothiophene-3-carboxylate; Ethyl 2-(acetylamino)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate(37.0 g, 138 mmol), sulfur (8.9 g, 277 mmol), and dimethyl phthalate (53.8 g, 277 mmol) were heated at 195C for -8 h. The clear solution was allowed to cool EPO <DP n="56"/>overnight to room temperature. Upon returning, a solid cake had formed in the flask and the stirring had stopped. Several unsuccessful attempts were made to get the solid in an easily filtered form. The solid was re-slurried in ethanol (200 mL) and filtered. The solid was then heated in ethanol (500 mL), cooled, and filtered again. Finally, it was heated in toluene with a Dean-Stark trap and filtered. The solid was then dried in a vacuum oven to yield a light yellow solid (12.7 g). A second crop (5.9 g) was obtained by concentrating the toluene filtrate.The two crops were then deacylated in separate runs by heating in toluene (-0.38 M in substrate) at reflux with pyrrolidine (5 equiv) for -4 h. Upon completion, the reaction mixtures were combined, concentrated to -100 mL, and filtered to remove a small amount of particles. The deep red filtrate was poured onto a Biotage 75L silica gel column and purified via gradient chromatography (10% EtOAc to 25% EtOAc in hexane). The fractions containing the desired product were combined and concentrated to yield a white solid (10.4 g, 34% over two steps). 1H NMR (DMSO-d6) δ 7.93 (s, 2H), 7.92 (d, 1H), 7.57 (d, 1H), 7.22 (t, 1H), 7.03 (t, 1H), 4.28 (q, 2H), 1.33 (t, 3H), LCMS RT = 3.13 min, [M+H]+ = 222.0.
 

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