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| | ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE Basic information |
| | ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE Chemical Properties |
| Melting point | 114-116 °C(lit.) | | Boiling point | 407.5±45.0 °C(Predicted) | | density | 1.235±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | | pka | 0.53±0.20(Predicted) | | form | Fine Crystalline Powder | | color | Yellow | | InChI | InChI=1S/C11H15NO2S/c1-2-14-11(13)9-7-5-3-4-6-8(7)15-10(9)12/h2-6,12H2,1H3 | | InChIKey | CDYVTVLXEWMCHU-UHFFFAOYSA-N | | SMILES | C12CCCCC=1C(C(OCC)=O)=C(N)S2 | | CAS DataBase Reference | 4506-71-2(CAS DataBase Reference) |
| | ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE Usage And Synthesis |
| Chemical Properties | yellow fine crystalline powder | | Uses | Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate was used in the preparation of:
- thienopyrimidine derivatives
- azo dyes
- N-(3-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-2-aryl hydrazono-3-oxobutanamide derivatives
- tetrahydrobenzo[b]thiophene dyes
| | Synthesis | GENERAL METHOD: Cyclohexanone (1 mmol), ethyl cyanoacetate (1 eq.), morpholine (1 eq.), and elemental sulfur (1 eq.) were dissolved in 5 mL of ethanol at 0°C and the reaction was stirred overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was extracted three times with ethyl acetate, the organic layers were combined and dried over anhydrous sodium sulfate. After drying, the solvent was again evaporated under reduced pressure. The final product was obtained as purified ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate by recrystallization from a mixed methanol/water solvent as a yellow crystalline solid. Yield: 98%, melting point 134-135 °C. 1H NMR (400 MHz, DMSO-d6) δ 1.20 (3H, t, J = 7.1 Hz, CH3), 1.60-1.65 (4H, m, CH2), 2.35-2.37 (2H, m, CH2), 2.55-2.56 (2H, m, CH2), 4.11 (2H , q, J = 7.3 Hz, OCH2CH3), 7.14 (2H, br s, NH2).13C NMR (100 MHz, DMSO-d6) δ 14.18 (CH3), 22.34 (CH2), 22.76 (CH2), 23.88 (CH2), 26.49 (CH2), 58.71 (OCH2), 103.16 (Cq), 115.96 (Cq), 131.50 (Cq), 163.19 (Cq), 165.32 (C=O). | | References | [1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4228 - 4240
[2] Synthetic Communications, 2010, vol. 40, # 14, p. 2067 - 2074
[3] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 619 - 634
[4] Journal of Sulfur Chemistry, 2014, vol. 35, # 3, p. 261 - 269
[5] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3171 - 3172 |
| | ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE Preparation Products And Raw materials |
| Raw materials | Sulfur-->Ethyl cyanoacetate-->Piperidine-->Cyclohexanone-->Ethanol-->Morpholine | | Preparation Products | 4-((3-(ethoxycarbonyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)amino)-4-oxobutanoic acid-->[1]Benzothieno[2,3-d]pyrimidin-4(1H)-one, 2,3,5,6,7,8-hexahydro-3-(3-methoxyphenyl)-2-thioxo--->[1]Benzothieno[2,3-d]pyrimidin-4(1H)-one, 2,3,5,6,7,8-hexahydro-3-(2-methoxyphenyl)-2-thioxo- |
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