Structure of 59804-25-0
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CAS No. : | 59804-25-0 |
Formula : | C9H9NO5S2 |
M.W : | 275.30 |
SMILES Code : | COC(=O)C1=C(O)C2=C(C=CS2)S(=O)(=O)N1C |
MDL No. : | MFCD08460400 |
InChI Key : | OKNMAOBDSCJUDO-UHFFFAOYSA-N |
Pubchem ID : | 54690599 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
EXAMPLE 10 By reacting 3-pyridylamine with 3-carbomethoxy-4-hydroxy-2-methylthieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-N-(3-pyridyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 241-244 C (recrystallization from pyridine). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; | 1.9 G. of 3-carbomethoxy-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide are suspended together with 0.9 g. of 2-aminothiazole in 250 ml. of absolute xylene and heated to reflux for 7 hours, by which means 150 ml. of xylene are slowly distilled off. The residual xylene is then evaporated in vacuo. The crystalline residue is recrystallized from ethanol. There is obtained 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide1,1-dioxide of melting point 217 C. (decomposition). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 11 By reacting 4-pyridylamine with 3-carbomethoxy-4-hydroxy-2-methylthieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-N-(4-pyridyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 263-267 C (recrystallization from dimethylformamide). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.9% | In 5,5-dimethyl-1,3-cyclohexadiene; for 6h;Reflux; | 5.4 g of TNXK-3, 300 ml xylene and 1.4g 2-aminopyridine in xylene solution 2.8 ml heating to reflux. After stirring reaction 6 hours, cooling. the majority of the solvent is removed under reduced pressure, cooling, filtering, the filter cake by adding 15 ml in water, adding sodium hydroxide 1 g and methanol 55 ml, heating the solvent, used to decolorize with active carbon, the filtrate is adjusted to PH hydrochloric acid 3, is cooled and is filtered, the filter cake is benzodioxane recrystallized, to get the yellow solid 4.2 g, yield 76.9%. |
EXAMPLE 9 By reacting 2-pyridylamine with 3-carbomethoxy-4-hydroxy-2-methylthieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 209-213 C (recrystallization from xylene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 20 By reacting 2-amino-pyrimidine with 3-carbomethoxy-4-hydroxy-2-methyl-thieno[2,3-e]-1,2-thiazine 1,1-dioxide for 18 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-N-(2-pyrimidinyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 221-223 C (recrystallisation from ethanol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 15 By reacting aminopyrazine with 3-carbomethoxy-4-hydroxy-2-methylthieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-N-pyrazinyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 245-248 C (recrystallization from xylene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 18 By reacting 2-amino-6-methyl-pyridine with 3-carbomethoxy-4-hydroxy-2-methyl-thieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-N-(6-methyl-2-pyridyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 216-218 C (recrystallisation from benzene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 17 By reacting 4-amino-2,6-dimethyl-pyrimidine with 3-carbomethoxy-4-hydroxy-2-methyl-thieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained N-(2,6-dimethyl-4-pyrimidinyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 270-271 C (recrystallisation from xylene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 12 By reacting 4-hydroxyaniline with 3-carbomethoxy-4-hydroxy-2-methylthieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 4,4'-dihydroxy-2-methyl-2H-thieno-[2,3-e]-1,2-thiazine-3-carboxanilide 1,1-dioxide of decomposition point 287-290 C (recrystallization from dioxane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 14 By reacting 3-chloroaniline with 3-carbomethoxy-4-hydroxy-2-methylthieno[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 3'-chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxanilide 1,1-dioxide of decomposition point 241-243 C (recrystallization from xylene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.2 G. of 3-(N-carbethoxymethyl-N-methyl-sulfamoyl)-thiophene-2-carboxylic acid methyl ester are suspended in 42 ml. of a 1-N methanolic sodium methylate solution in the cold and under a nitrogen stream. After stirring for 15 minutes, a clear solution results. The solution is heated to reflux for 20 minutes, then cooled, neutralized and evaporated in vacuo. The residue is taken up in methylene chloride, shaken once each time with water and a sodium bicarbonate solution, dried and evaporated. The residue is brought to crystallization with methanol. There is obtained 3-carbomethoxy-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine1,1-dioxide of melting point 193-195 C. | ||
13.2 G. (0.041 mol) of the obtained 3-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester are suspended in 42 ml. of a 1-N methanolic sodium methylate solution in the cold and under a nitrogen atmosphere, everything dissolving after stirring for 15 minutes. The solution is heated to reflux for 25 minutes, cooled, neutralized with concentrated hydrochloric acid and evaporated in vacuo. The residue is taken up in methylene chloride, shaken out once each time with water and a 5% sodium bicarbonate solution, dried and evaporated. The crystalline residue is digested with a small amount of methanol for purification. There is obtained 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine1,1-dioxide of melting point 193-195 C., which can be converted by reaction with 2-aminothiazole in a manner analogous to that described in the last part of Example 1 into the 4-hydroxy-2-methyl-N-(2-thiazoly)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide1,1-dioxide of melting point 217 C (decomposition). | ||
2.41 G. (0.010 mol) of the obtained 3-chlorosulfonylthiophene-2-carboxylic acid methyl ester are dispersed together with 1.53 g. of sarcosine ethyl ester hydrochloride in 10 ml. of absolute pyridine and stirred at room temperature. After 2 hours, the mixture is poured on to 50 ml. of ice-cold 2-N hydrochloric acid and extracted five times with 20 ml. of methylene chloride each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated. The crystalline residue is digested with a small amount of ice-cold ethanol. 13.2 G. (0.041 mol) of the obtained 3-(N-carbethoxymethyl-N-methylsulfamoyl)-thiophene-2-carboxylic acid methyl ester are suspended in 42 ml. of a 1-N methanolic sodium methylate solution in the cold and under a nitrogen atmosphere, everything dissolving after stirring for 15 minutes. The solution is heated to reflux for 25 minutes, cooled, neutralized with concentrated hydrochloric acid and evaporated in vacuo. The residue is taken up in methylene chloride, shaken out once each time with water and a 5% sodium bicarbonate solution, dried and evaporated. The crystalline residue is digested with a small amount of methanol for purification. There is obtained 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine1,1-dioxide of melting point 193-195 C., which can be converted by reaction with 2-aminothiazole in a manner analogous to that described in the last part of Example 1 into the 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide1,1 -dioxide of melting point 217 C (decomposition). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; | EXAMPLE 3 A solution of 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide (1.0 g) and 5-amino-2-hydroxytropone (0.55 g) in xylene (25 ml) was refluxed for 21 hours and the reaction mixture was allowed to stand at ambient temperature. The crystals were collected by filtration, washed with toluene and recrystallized from N,N-dimethylformamide to give 4-hydroxy-2-methyl-N-(2-hydroxy-1-oxo-2,4,6-cycloheptatrien-5-yl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide (0.82 g). mp: 231-232 C. IR (Nujol): 3600, 3350, 3250, 1645, 1605, 1530, 1200 cm-1 NMR (NaOD+D2 O+CD3 OD, δ): 3.00 (3H, s), 7.0-7.8 (6H, m) Analysis Calcd. for C15 H12 N2 O6 S2 *0.5H2 O: Calcd.: C, 46.27; H, 3.62; N, 7.19. Found: C, 46.16; H, 3.63; N, 7.31. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 5,5-dimethyl-1,3-cyclohexadiene; | EXAMPLE 2 A solution of 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine, 1,1-dioxide (1.0 g) and 2-amino-5-chlorotropone (0.62 g) in xylene (25 ml) was refluxed for 21 hours and the reaction mixture was allowed to stand at ambient temperature. The crystalline precipitates were collected by filtration and washed twice with toluene to give 4-hydroxy-2-methyl-N-(5-chloro-1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide (1.22 g). mp: 243-245 C. IR (Nujol): 3260, 1645, 1605, 1560, 1510, 1350 cm-1 Analysis Calcd. for C15 H11 ClN2 O5 S2: Calcd.: C, 45.17; H, 2.78; N, 7.02. Found: C, 45.07; H, 3.01; N, 7.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 19 By reacting 5-amino-1,2,3,4-tetrazole with 3-carbomethoxy-4-hydroxy-2-methyl-thieno[2,3-e]-1,2-thiazine 1,1-dioxide for 14 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-N-(1,2,3,4-tetrazol-5-yl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 224 C (recrystallisation from ethanol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 16 By reacting 5-amino-3,4-dimethyl-isoxazole with 3-carbomethoxy-4-hydroxy-2-methyl-thieno[2,3-e]-1,2-thiazine 1,1-dioxide for 14 hours in a manner analogous to that described in Example 1, there is obtained N-(3,4-dimethyl-5-isoxazolyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide of decomposition point 206-208 C (recrystallisation from benzene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aniline; | EXAMPLE 8 By reacting aniline with 3-carbomethoxy-4-hydroxy-2-methyl-thieno-[2,3-e]-1,2-thiazine 1,1-dioxide for 7 hours in a manner analogous to that described in Example 1, there is obtained 4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxanilide 1,1-dioxide of decomposition point 248-251 C. (recrystallization from xylene). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium hydroxide; In methanol; at 20.0℃; for 3.0h; | 5.3 g of TNXK-3 and 20 ml of methanol were added to a reaction flask. Stir at room temperature. Separately add dimethyl sulfate 3.7 g methanol (5 ml) solution and 50% sodium hydroxide solution (5 ml). After the completion of the dropping, room temperature reaction 3 hours, cooling to 10 degrees, the water 50 ml dilution, use 10% hydrochloric acid to the PH is 3. Filtering, the filter cake after the water washing, drying, recrystallization with methanol, 60 degrees decompression drying, getting white solid 4.8 g, yield 86%. |
3.6 g | With sodium hydroxide; In methanol; at 20.0℃; for 3.5h; | 3) Weigh 4g of crude product II'(15.3mmol) and dissolve it in 20ml of methanol, add dropwise 2.8g of dimethyl sulfate (21.9mmol) in methanol (5ml) and 50% sodium hydroxide solution ( 4ml). After the dripping is completed, react for 3.5h at room temperature, then cool to 10C, add 40ml of water to dilute and adjust the pH to 3 with 10% hydrochloric acid. After suction filtration, the filter cake was washed with water 3 times and dried, and then recrystallized with methanol, and dried under reduced pressure at 60 C. to obtain an off-white solid ester compound II (3.6 g, 78.7%) containing a thiazine ring. |
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