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CAS No. : | 2810-04-0 | MDL No. : | MFCD00005436 |
Formula : | C7H8O2S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JZGZKRJVTIRPOK-UHFFFAOYSA-N |
M.W : | 156.20 | Pubchem ID : | 76052 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With sodium hydride; In 1,4-dioxane; for 2h;Reflux; | General procedure: A methyl ketone (1 eq.) was added to dry 1,4-dioxane and NaH (60 % oil suspension, 5eq.) was added in portions to the mixture in an ice-bath. The resulting mixture was stirred atroom temperature for 1 h. The required ester (5 eq.) was added to the mixture and refluxed for1 h. After cooling, 10 % HCl solution was added to the reaction mixture and extracted withCH2Cl2 (3×20 mL). The crude product was dried over MgSO4. Recrystallization or columnchromatography gave the product, which was dried in vacuo (25 C, 0.5 mbar), affordingspectroscopically pure product.12 More details of the syntheses of the individual products andtheir spectral data are given in the Supplementary material to this paper. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.54 g (93%) | With sodium; In ethanol; | EXAMPLE 40 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong>-1-N-t-butylcarboxamide 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> was first prepared according to the procedure of Example 1B, using <strong>[5654-97-7]7-azaoxindole</strong> (1.5 g, 11.2 mmol), sodium (1.3 g, 56.5 mmol), ethanol (25 mL), and ethyl-thiophene-2-carboxylate (3 mL, 22.3 mmol). Yield: 2.54 g (93%). The title compound was prepared from 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> according to the procedure of Example 1C, using 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> (500 mg, 2.0 mmol), t-butyl isocyanate (0.35 mL, 3.0 mmol), triethylamine (0.6 mL, 4.4 mmol) and DMSO (10 mL). The crude product was purified by flash chromatography on silica gel using 9:1 chloroform/methanol and recrystallized from methanol/chlorform. Yield: 70 mg (25%). 1 H NMR (DMSO-d6): delta9.34 (s, 1H), 8.81 (d, J=3.5 Hz, 1H), 8.54 (d, J=8.0 Hz, 1H), 7.91-7.87 (m, 2H), 7.25-7.18 (m, 2H), 1.41 (s, 9H). MS m/e (relative percent) 343 (35), 244 (81), 160 (100), 111 (9). IR (KBr disc) 1718, 1654, 1629, 1607, 1554, 1534, 1497, 1433 cm-1. Analysis calc'd for C17 H17 N3 O3 S: C 59.46, H 4.99, N 12.24; found: C 59.24, H 4.77, N 12.14. M.p.>250 C. |
2.54 g (93%) | With sodium; In ethanol; | Example 40 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong>-1-N-t-butylcarboxamide 3-(2-Thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> was first prepared according to the procedure of Example 1B, using <strong>[5654-97-7]7-azaoxindole</strong> (1.5 g, 11.2 mmol), sodium (1.3 g, 56.5 mmol), ethanol (25 mL), and ethyl-thiophene-2-carboxylate (3 mL, 22.3 mmol). Yield: 2.54 g (93%). The title compound was prepared from 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> according to the procedure of Example 1C, using 3-(2-thenoyl)-<strong>[5654-97-7]7-azaoxindole</strong> (500 mg, 2.0 mmol), t-butyl isocyanate (0.35 mL, 3.0 mmol), triethylamine (0.6 mL, 4.4 mmol) and DMSO (10 mL). The crude product was purified by flash chromatography on silica gel using 9:1 chloroform/methanol and recrystallized from methanol/chlorform. Yield: 70 mg (25%). 1H NMR (DMSO-d6): delta 9.34 (s, 1 H), 8.81 (d, J = 3.5 Hz, 1 H), 8.54 (d, J = 8.0 Hz, 1 H), 7.91-7.87 (m, 2 H), 7.25-7.18 (m, 2 H), 1.41 (s, 9 H). MS m/e (relative percent) 343 (35), 244 (81), 160 (100), 111 (9). IR (KBr disc) 1718, 1654, 1629, 1607, 1554, 1534, 1497, 1433 cmmin1. Analysis calc'd for C17H17N3O3S: C 59.46, H 4.99, N 12.24; found: C 59.24, H 4.77, N 12.14. M.p. > 250C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
607 mg (79%) | In ethanol; | B. 5,6-Dichloro-3-(2-thenoyl)-4-azaoxindole Pellets of sodium metal (0.29 g, 12.6 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid <strong>[136888-26-1]5,6-dichloro-4-azaoxindole</strong> (500 mg, 2.46 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.67 mL. 5.0 mmol). The mixture was heated at reflux for one day under nitrogen. The mixture was cooled, poured into ice/water and acidified to pH 3 with 6N HCl solution. The title compoundcompound was collected by filtration and dried in vacuo to afford 607 mg (79%). |