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CAS No. : | 19418-11-2 | MDL No. : | MFCD11520782 |
Formula : | C5H8O2S | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | MZOYMQRKTJRHGJ-UHFFFAOYSA-N |
M.W : | 132.18 | Pubchem ID : | 443066 |
Synonyms : |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-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 thionyl chloride; | EXAMPLE 27 1-[N-(2-Tetrahydrothienyl)carbamoyl]-5-fluorouracil Thionyl chloride (16.5 g.) was added to <strong>[19418-11-2]2-tetrahydrothiophenecarboxylic acid</strong> (12.2 g.) at ambient temperature and heated for 2 hours at 80 C. The reaction mixture was evaporated to dryness under reduced pressure and the residual oil was fractionated by distillation in vacuo to give <strong>[19418-11-2]2-tetrahydrothiophenecarboxylic acid</strong> chloride (9.79 g.), (b.p. 46 C./1 mmHg). | |
With thionyl chloride; In dichloromethane; at 20℃; for 3h; | Step 1 Methoxymethyltetrahydrothiophene-2-carboxylamide 32.0 ml (0.44 mol; 1.27 eq) of thionyl chloride were added dropwise, at ambient temperature, over the course of 15 minutes, to a solution of 46.0 g (0.35 mol; 1.0 eq) of <strong>[19418-11-2]tetrahydrothiophene-2-carboxylic acid</strong> (commercial) in 200 ml of dichloromethane. The reaction medium was stirred at ambient temperature for 3 hours until no more gas was given off. The dichloromethane and the excess thionyl chloride were evaporated off under vacuum and the residue was co-evaporated three times with 100 ml of toluene. The acid chloride obtained was solubilized in 200 ml of dichloromethane, and 37.34 g (0.38 mol; 1.1 eq) of N,O-dimethylhydroxylamine hydrochloride were added. The reaction medium was cooled to -10 C. and a mixture of 116 ml (0.84 mol; 2.4 eq) of triethylamine in 100 ml of dichloromethane was added dropwise over the course of one hour (while maintaining the temperature below 5 C.). After the addition, the reaction medium was stirred at ambient temperature for one hour and was then washed with 250 ml of a 1 M aqueous hydrochloric acid solution. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with 200 ml of a 1 M aqueous sodium hydrogen phosphate solution, dried over anhydrous magnesium sulfate, filtered and evaporated. 51.0 g of methoxymethyltetrahydrothiophene-2-carboxylamide were obtained in the form of an orange oil. Yield=84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred suspension of potassium bufoxide in THF is added TOSMIC (tosylmethylisocyanide, 3.9 g) at 7-10 C. This is followed by 1.92 g thiolactam in 20 ml THF. After 5 minutes, 2 ml acetic acid is dripped in. The solution is concentrated, taken up in water, and extracted with methylene chloride. The combined organic residue is dried and concentrated, then 40 ml 2N HCl added and refluxed 12 hours. The solution is made basic and extracted with ether. The aqueous layer is taken to pH 1, extracted again with ether and these organics combined, dried, and concentrated to give the product tetrahydrothienylcarboxylic acid, mp 95-98 C. |
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