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CAS No. : | 6326-83-6 | MDL No. : | MFCD00004357 |
Formula : | C5H6O4S3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GQECANUIPBFPLA-UHFFFAOYSA-N |
M.W : | 226.29 | Pubchem ID : | 80618 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
82% | With sodium hydroxide; In water; for 10h;Reflux; | To a water (20 mL) solution of <strong>[33906-30-8]2-hydrazino-benzoic acid hydrochloride</strong> (2.508 g, 13.30 mmol) was added water solution of sodium hydroxide (1.029 N, d=1.040, 26.81 g, 26.60 mmol) followed by bis(carboxymethyl)trithiocarbonate (3.006 g, 13.28 mmol). The mixture was stirred at reflux temperature for 10 h, cooled to room temperature and stirred for 50 h. The solid product was filtered off and washed on funnel successively with water (2×10 ml), ether (5 mL) and hexane (20 mL). The material was dried in a vacuum oven at 80 C. for 5 h to afford 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (2.93 g, 82%) as a solid. 1H NMR (400 MHz, DMSO-d6): delta 4.33 (1H, bs), 6.66 (1H, m), 6.90 (1H, m), 7.40 (1H, m), 7.89 (1H, m), 13.37 (1H, bs). ESI-MS: 267.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | General procedure: A constantly stirred suspension of appropriately 5-substituted phenyl-1,3,4-thiadiazol-2-amines (4a-4f, 1 equiv.) in water (5 mL) was heated at 95C for 1-2 h. To this, bis (carboxyl methyl) trithiocarbonate (1.1 equiv.) was slowly added and heating was continued at 100C for 12-18 h. After cooling to room temperature, the precipitated solid was filtered and washed with cold water. The dried solid was purified by flash silica column [gradual eluent: EtOAc/petroleum ether, 0-50%] to afford the 3-(5-substitutedphenyl)-1,3,4-thiadiazol-2-yl)-2-thioxothiazolidin-4-one derivatives (5a-5f). |
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