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Chemical Structure| 7311-95-7

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Product Details of [ 7311-95-7 ]

CAS No. :7311-95-7
Formula : C11H11NO2S
M.W : 221.28
SMILES Code : O=C(C1=C(N)SC2=CC=CC=C21)OCC
MDL No. :MFCD00102506
InChI Key :XNASJEQIJMDBQN-UHFFFAOYSA-N
Pubchem ID :699464

Safety of [ 7311-95-7 ]

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

Application In Synthesis of [ 7311-95-7 ]

* 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 [ 7311-95-7 ]

[ 7311-95-7 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 7311-95-7 ]
  • [ 60100-09-6 ]
  • [ 18774-49-7 ]
YieldReaction ConditionsOperation in experiment
83% Reflux; General procedure: The different ethyl 2-aminothiophene-3-carboxylate (5a-g) (1 eq.) and formamide (3.2mL/mmol eq.) were refluxed for 8 h. The reaction mixture was then cooled in an ice-bath and added of cold water. The precipitate formed was collected by filtration, washed thoroughly with cold water and purified by crystallisation from EtOH/H2O unless otherwise stated.
  • 2
  • [ 7311-95-7 ]
  • [ 7238-62-2 ]
  • [ 122945-79-3 ]
  • 3
  • [ 7311-95-7 ]
  • 2-methylsulfanyl-3-phenyl-3<i>H</i>-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-4-one [ No CAS ]
  • 5
  • [ 7311-95-7 ]
  • 3-(4-methoxy-phenyl)-2-methylsulfanyl-3<i>H</i>-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-4-one [ No CAS ]
  • 6
  • [ 7311-95-7 ]
  • 3-(4-fluoro-phenyl)-2-methylsulfanyl-3<i>H</i>-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-4-one [ No CAS ]
  • 7
  • [ 7311-95-7 ]
  • (4-oxo-3-phenyl-3,4-dihydro-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-2-ylsulfanyl)-acetonitrile [ No CAS ]
  • 8
  • [ 7311-95-7 ]
  • 3-(4-ethoxy-phenyl)-2-methylsulfanyl-3<i>H</i>-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-4-one [ No CAS ]
  • 9
  • [ 7311-95-7 ]
  • [3-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-2-ylsulfanyl]-acetonitrile [ No CAS ]
  • 10
  • [ 7311-95-7 ]
  • 3-benzo[1,3]dioxol-5-yl-2-methylsulfanyl-3<i>H</i>-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-4-one [ No CAS ]
  • 11
  • [ 7311-95-7 ]
  • [3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-2-ylsulfanyl]-acetonitrile [ No CAS ]
  • 12
  • [ 7311-95-7 ]
  • [3-(4-dimethylamino-phenyl)-4-oxo-3,4-dihydro-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-2-ylsulfanyl]-acetonitrile [ No CAS ]
  • 13
  • [ 7311-95-7 ]
  • 2-methylsulfanyl-3-(4-trifluoromethoxy-phenyl)-3<i>H</i>-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-4-one [ No CAS ]
  • 14
  • [ 7311-95-7 ]
  • [3-(4-ethoxy-phenyl)-4-oxo-3,4-dihydro-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-2-ylsulfanyl]-acetonitrile [ No CAS ]
  • 15
  • [ 7311-95-7 ]
  • (3-benzo[1,3]dioxol-5-yl-4-oxo-3,4-dihydro-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-2-ylsulfanyl)-acetonitrile [ No CAS ]
  • 16
  • [ 7311-95-7 ]
  • [4-oxo-3-(4-trifluoromethoxy-phenyl)-3,4-dihydro-benzo[4,5]thieno[2,3-<i>d</i>]pyrimidin-2-ylsulfanyl]-acetonitrile [ No CAS ]
  • 17
  • [ 7311-95-7 ]
  • 2-Thioxo-2,3-dihydro-1H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one [ No CAS ]
  • 18
  • [ 7311-95-7 ]
  • [ 257611-24-8 ]
  • 19
  • [ 7311-95-7 ]
  • [ 142310-66-5 ]
  • 20
  • [ 7311-95-7 ]
  • [ 257611-16-8 ]
  • 21
  • [ 7311-95-7 ]
  • [ 257611-01-1 ]
  • 22
  • [ 7311-95-7 ]
  • 2-{3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propylsulfanyl}-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one [ No CAS ]
  • 23
  • [ 7311-95-7 ]
  • Potassium; 4-oxo-3,4-dihydro-benzo[4,5]thieno[2,3-d]pyrimidine-2-thiolate [ No CAS ]
  • 24
  • [ 7311-95-7 ]
  • [ 40143-03-1 ]
  • 25
  • [ 7311-95-7 ]
  • [ 7127-28-8 ]
  • 26
  • [ 7311-95-7 ]
  • [ 40143-00-8 ]
  • 28
  • [ 7311-95-7 ]
  • [ 40142-93-6 ]
  • 30
  • [ 7311-95-7 ]
  • [ 40142-96-9 ]
  • 31
  • [ 7311-95-7 ]
  • [ 221061-08-1 ]
YieldReaction ConditionsOperation in experiment
90% With N-Bromosuccinimide; In chloroform; for 1.0h; To a solution of lc (760 mg, 3.44 mmol) in [CHC13] (10 mL) was added N bromosuccinimide (673 mg, 3.78 mmol). The resultant mixture was stirred for 1 h, then mixed with saturated [NAHC03] solution (100 mL), and extracted with methylene chloride (100 mL, 3x). The combined organic phases were dried over [MGS04,] filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4: 1) then provided the title compound (930 mg, 90%) as a yellow solid: MS (ES) [M/Z] [300] (M+H) + [; 1H] NMR (400 MHz, [CDC13)] [87.] 96 (d, J= 8. 8 Hz, 1 H), 7.63 (s, 1 H), 7.42 (d, J= 8.8 Hz, 1H), 6.52 (brs, 2 H), 4.42 (q, J= 7.2 Hz, 2 H), 1.48 (t, J= 7.2 Hz, 3 H).
82% With N-Bromosuccinimide; In chloroform; To a solution of 21 (2.00 g, 9.03 mmol) in chloroform (20.0 mL) was added N-bromosuccineimide (1.61 g, 9.03 mmol) and the mixture was stirred overnight. The solvent was removed in vacuo, the residue was added chloroform and n-hexane. The resulting precipitate was dissolved in ethyl acetate. The solution was washed with sat. sodium bicarbonate aqueous solution, water and brine, then dried over anhydrous magnesium sulfate. After the filtration, the filtrate was concentrated in vacuo to obtain ethyl 2-amino-6-bromo-1-benzothiophene-3-carboxylate (2.21 g, 82%) as a off-white powder. 1H NMR (200 MHz, DMSO-d6): δ 1.34 (3H, t, J = 7.0 Hz), 4.30 (2H, q, J = 7.0 Hz), 7.35-7.44 (1H, m), 7.83-7.92 (2H, m), 8.03 (2H, brs); MS (ESI): m/z 298 [M-H]-.
68% With N-Bromosuccinimide; In chloroform; Step 4; Preparation of ethyl 2-amino-6-bromo-l-benzothiophene-3-carboxylate; Ethyl 2-amino-1-benzothiophene-3-carboxylate (10.4 g, 44.7 mmol) was dissolved in chloroform (100 mL) and treated with NBS (7.95 g, 44.7 mmol). Upon completion of the reaction, a light tan solid precipitated from the mixture. The slurry was concentrated to -30% of the original volume on a rotavap and then filtered. The solid was slurried in EtOAc (300 mL) and treated with satd NaHCO3 (200 mL) to obtain two clear phases. The organic phase was washed further with satd NaHCO3 (4X~200mL) and water (200 mL). The organic layer was collected, dried with sodium sulfate, filtered, and concentrated to yield an off-white solid (9.1 g, 68%). 1H NMR (DMSO-d6) δ 8.00 (s, 2H), 7.85 (s, 1H), 7.83 (d, 1H), 7.36 (d, 1H), 4.28 (q, 2H), 1.33 (t, 3H).
  • 32
  • [ 7311-77-5 ]
  • [ 7311-95-7 ]
YieldReaction ConditionsOperation in experiment
85% With pyrrolidine; In toluene; at 100℃; for 8.0h; To a solution of lb (1.06 g, 4.03 mmol) in toluene (100 mL) was added pyrrolidine (5 mL). The resultant mixture was heated at [100 C] for 8 h, diluted with brine solution (200 mL) and extracted with ethyl ether (300 mL, 3x). The combined organic phases were dried over [MGS04,] filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 4: 1) then afforded the title compound (0.76 g, 85%) as a yellow solid: MS [(ES) M/Z] 222 [(M+H) + ; LH] NMR (400 MHz, [CDC13)] 88. 14 (d, J= 8.0 Hz, 1 H), 7.53 (d, J= 7.2 Hz, 1H), 7.28 (m, 1 H), 7.04 [(M,] 1 H), 6.51 (brs, 2 H), 4.45 (q, [J= 7. 2 HZ, 2 H),] 1.50 (t, [J= 7. 2 HZ, 3 H).]
55% With pyrrolidine; In toluene; at 100℃; for 23.0h; To a stirred suspension of 2-acetylamino-benzo [b] thiophene-3-carboxylic acid ethyl ester (Compound No. 516 of Table 134, prepared as described in Example 27; 85mg, 0.323 mmol) in toluene (15ml) was added pyrrolidine (400u. l). The reaction mixture was heated at 100C for 6 hours, then further pyrrolidine (400u. l) was added and heating continued at 100C for 17 hours. The mixture was allowed to cool to room temperature, quenched with brine and extracted with ether. The combined organic extracts were dried over magnesium sulphate and evaporated to dryness under reduced pressure to give an off- white solid (104mg). Chromatography of the crude material, using 20% ether in hexane (by volume) as eluant, gave the desired product as a white solid (39mg, 55%). 'H NMR 8H (400MHz, CDC13) : 8.10 (1H, d), 7.50 (1H, d), 7.30 (1H, t), 7.10 (1H, t), 6.50 (2H, br s), 4.40 (2H, q) and 1.45 (3H, t) ppm.
  • 33
  • [ 7311-95-7 ]
  • [ 202591-85-3 ]
  • 2-(but-2-ynyloxycarbonylamino)-benzo[b]thiophene-3-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% In 1,4-dioxane; at 20℃; for 65.0h; To a stirred solution of aminothiophene UO (lOOmg, 0.45 mmol) in 1,4-dioxane (10ml) was added 2-butynyl chlorofonnate (60p1, 0.5 mmol). The reaction mixture was stirred at room temperature for 65 hours and then evaporated to dryness under reduced pressure to give a brown solid (114mg). Chromatography of the crude product, using 25% ether in hexane (by volume) as eluant, gave the desired product as an off-white solid (1 1mg, 8%). lH NMR 5H (400MHz, CDC13) : 11.10 (1H, br s), 8.25 (1H, d), 7.70 (1H, d), 7.40 (1H, t), 7. 30 (1H, t), 4.85 (2H, m) 4.45 (2H, q), 1.90 (3H, m) and 1.50 (3H, t) ppm.
  • 34
  • [ 7311-95-7 ]
  • [ 18774-50-0 ]
YieldReaction ConditionsOperation in experiment
95% To a solution of 2-amino-benzo[b]thiophene-3-carboxylic acid ethyl ester (5.24 g, 23.6 mmol) in ethanol-tetrahydrofuran (1:1, 60.0 mL) was added 2 M aqueous sodium hydroxide solution (60.0 mL) at room temperature, and the mixture was refluxed for 8 h. After the removing solvents in vacuo, the residue was added water and 2 M aqueous hydrochloric acid solution to adjusted pH 5.0. The resulting precipitate was obtained by filtration, washed with water and dried in vacuo to give 22 (4.34 g, 95%) as a pink powder. 1H NMR (600 MHz, DMSO-d6): δ 7.00-7.07 (1H, m), 7.18-7.25 (1H, m), 7.58 (1H, d, J = 7.3 Hz), 7.92 (2H, br s), 7.95-8.02 (1H, m), 12.28 (1H, br s); MS (ESI): m/z 191 [M-H]+.
13% With potassium hydroxide; ethanol; water; for 0.333333h;Heating / reflux; Ethyl 2-amino-1-benzothiophene-3-carboxylate (obtained according to procedures described in Hallas, G.; Towns, A.D., Dyes and Pigments (1997), 35,219-237) (10 g, 40.0 mmol) was suspended in ethanol (100 ml_), and heated to reflux. A solution of potassium hydroxide (KOH, 8.4 g) in water (100 ml_) was added over the period of 10 minutes. The reaction mixture was refluxed for another 10 minutes, cooled to room temperature, and filtered. The collected solid was washed with water to pH neutral to give the title compound as a brown solid (1.0 g, 13.0 % yield). ESMS [M+H]+m/z 194.2.
An aq. solution of NaOH (IM, 20 mL) was added to a solution of ethyl 2-amino-l- benzothiophene-3-carboxylate (0.66 g, 3.00 mmol) in dioxane (10 mL) and the reaction mixture was heated at 1000C for 2 h. The reaction mixture was concentrated in vacuo to leave an aqueous residue and then a 2M aq. solution of HCl was added such that the pH = 4 to give a precipitate. The mixture was filtered and the collected solid was washed with water to give the crude title compound (0.42 g, 72%). 1H NMR (400 MHz, DMSO/DMSO-d6)* ) δ 12.25 (s, IH), 7.95 (d, IH), 7.89 (s, 2H), 7.56 (d, IH), 7.22-7.17 (m, IH), 7.04-6.99 (m, IH); m/z (M-H)" 192.2.
  • 35
  • [ 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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