Reaktion #1534711

Reaktionsgleichung

4-hydroxy-N-(2-thiazolyl)-2H-thieno-[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

sodium hydride

methyl iodide

sodium

→

4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno-[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react for a further 1 hour
2. 2
   workup.DISTILLATIONAfter distillation of the solvent
3. 3
   SonstigeThe organic phase is separated
4. 4
   workup.STIRRINGshaken out with a total of 50 ml of a 0.5% sodium bicarbonate solution
5. 5
   Extraktionis back-extracted several times with methylene chloride
6. 6
   ExtraktionThe acidic aqueous phase is extracted with methylene chloride
7. 7
   Trocknenthe combined organic extracts dried over sodium sulphate
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe crystalline residue is digested with a small amount of cold ethanol for purification

Vorschrift

0.329 g (1 mmol) of 4-hydroxy-N-(2-thiazolyl)-2H-thieno-[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide are dissolved in 2 ml of absolute dimethylformamide and added at 0° C. to a stirred suspension of 0.026 g (1.1 mmol) of sodium hydride in 1 ml of absolute dimethylformamide. The mixture is stirred at room temperature for a further 1 hour. 0.1 ml (0.226 g; 1.6 mmol) of methyl iodide are then added to the sodium salt solution and allowed to react for a further 1 hour. After distillation of the solvent, the residue is taken up in 200 ml of methylene chloride and 10 ml of 0.5-N hydrochloric acid. The organic phase is separated and shaken out with a total of 50 ml of a 0.5% sodium bicarbonate solution. The aqueous layer, which now contains the desired product, is back-extracted several times with methylene chloride and acidified with hydrochloric acid. The acidic aqueous phase is extracted with methylene chloride and the combined organic extracts dried over sodium sulphate and evaporated. The crystalline residue is digested with a small amount of cold ethanol for purification. There is obtained 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno-[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of melting point 217° C. (decomposition).

Quelle