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CAS No. : | 2295-31-0 | MDL No. : | MFCD00005478 |
Formula : | C3H3NO2S | Boiling Point : | No data available |
Linear Structure Formula : | HNC(O)CH2SC(O) | InChI Key : | ZOBPZXTWZATXDG-UHFFFAOYSA-N |
M.W : | 117.13 | Pubchem ID : | 5437 |
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 |
---|---|---|
With sodium acetate; trichlorophosphate; In N-methyl-acetamide; dichloromethane; 1,2-dichloro-ethane; | REFERENCE EXAMPLE 4 Production of 2,4-dichloro-thiazol-4-yl-carboaldehyde of the formula STR22 To a solution of dimethylformamide (73.1 g) in dichloroethylene (200 ml) was added dropwise phosphorus oxychloride (122.7 g) under ice-cooling, followed by stirring for 30 minutes (for preparation of Vilsmeier reagent). The resultant solution was admixed with thiazolin-2,4-dione (23.4 g) and heated for 1 hour under refluxing. The reaction solution obtained was cooled to ambient temperature, poured onto ice (200 g), neutralized by addition of sodium acetate and then extracted 3 times with 200 ml-portions of methylene chloride. The resultant extract in methylene chloride was washed with a small volume of saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue obtained was purified chromatographically on a column of silica-gel as developed with benzene-ethyl acetate (10:1) as eluent. 4-Chloro-thiazol-5-yl-carboaldehyde (0.34 g) was afforded, and the titled compound (2.05 g) was also obtained as light yellow colored crystals. NMR, delta (CDCl3): 9.90 (1H, s) MS (m/e): 182 (M+ +1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium acetate; trichlorophosphate; In N-methyl-acetamide; dichloromethane; | REFERENCE EXAMPLE 3 Production of 4-chloro-thiazol-5-yl-carboaldehyde of the formula STR20 Phosphorus oxychloride (122.7 g) was added dropwise to dimethylformamide (73.1 g) under ice-cooling, and the mixture obtained was stirred for 30 minutes (for preparation of Vilsmeier reagent). The mixture was then admixed with thiazoline-2,4-dione STR21 (23.4 g), followed by heating at 100° C. for 3 hours. The reaction solution was cooled to ambient temperature, poured onto ice (200 g), neutralized by addition of sodium acetate and then extracted 4 times with 200 ml-portions of methylene chloride. The resultant extract in methylene chloride was washed with a small volume of saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was purified chromatographically on a column of silica gel as developed with benzene-ethyl acetate (10:1) as eluent. The titled compound (1.10 g) was obtained as light yellow colored crystals. NMR, delta (CDCl3): 8.93 (1H, d, J=1 Hz), 10.03 (1H, d, J=1 Hz). MS (m/e): 148 (M+ +1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(a) tert-Butyl [4'-(2,4-dioxothiazolidin-5-ylidenemethyl)biphenyl-3-ylmethyl]carbamate In a manner similar to that of Example 1(f) by reacting 7.4 g (24 mmol) of tert-butyl (4'-formyl-biphenyl-3-ylmethyl)carbamate (prepared as in Example 1(e) from tert-butyl (3-bromo benzyl)carbamate)with 2.8 g (24 mmol) of 2,4-thiazolidine dione, 9 g (95%) of the expected product are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 6h; | A mixture of 1,3-thiazolidine-2,4-dione (6, 1 mmol),<strong>[204205-33-4]2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone</strong> (7, 1 mmol) and sodium bicarbonate (2 equiv) were dissolved in DMF and stirred atambient temperature for 6 h. After completion of the reaction as evidenced by TLC (eluent 7:3 / hexane:ethyl acetate) the reaction mixture was poured into water (25 mL), extracted with ethyl aceate and the solvent distilled under vacuum to obtain pure 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With piperidine; acetic acid; In toluene; at 80℃;Dean-Stark; | Thiazolidine-2,4-dione 1g (0.008538 mol), 4-Fluoro-2-trifluoromethyl-benzaldehyde 1.640 g, Piperidine 0.422ml, acetic acid 0.182ml and toluene 20ml were added to the dean-stark apparatus at 80 C, After reacting for 12 hours or longer, it was recrystallized to obtain pure 5- (4-Fluoro-2-trifluoromethyl-benzylidene) -thiazolidine-2,4-dione. Yield: 78%. |
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