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CAS No. : | 53595-65-6 | MDL No. : | MFCD00067990 |
Formula : | C4H4BrNO2S2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | WXJQQLDICAOBJB-UHFFFAOYSA-N |
M.W : | 242.11 | Pubchem ID : | 1241304 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-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 |
---|---|---|
76.66% | With ammonia; In tetrahydrofuran; at -78℃; for 3h; | To solution of 3, 5-dichlorothiophene-2-sulfonyl chloride (6.2 g, 23.70 mmol) in THF (10 mL), saturated ammonia solution in THF (60 mL) was added at -78 C. The solid precipitated out and evaporated to dryness and the crude triturated with pentane to obtain the title compound, lnt-B-2.15 (4.4 g, 76.66 %). LCMS ESI(-ve) (m/z): 240.0 (M-2). |
68% | With ammonia; In 1,4-dioxane; water monomer; at 0℃; for 0.5h; | (143e) 5-Bromothiophene-2-sulfonamide 5-Bromothiophene-2-sulfonyl chloride (0.30 g, 1.2 mmol) was dissolved in 1,4-dioxane (2 mL). The resulting mixture was stirred at 0C, and 28% ammonia water (4 mL) was added thereto. The resulting mixture was stirred at 0C for 30 min. The reaction solvent was evaporated under reduced pressure, and water was added to the residue. After extraction with methylene chloride, the organic layer was washed with water and brine, and then dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 0.19 g (yield: 68%) of a crude product of the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm: 7.42 (1H, m), 7.06 (1H, m), 5.02 (2H, s). |
With ammonia; at 15℃; for 0.2h; | To a solution of 5-bromothiophene-2-sulfonyl chloride (2 g, 7.65 mmol, 1 eq) in ammonia (1.95 g, 115 mmol, 1.92 mL, 15 eq). The mixture was stirred at 15 C for 0.2 hour. TLC (petroleum ether/EtOAc = 3/1) indicated 5-bromothiophene-2-sulfonyl chloride was consumed completely and new spot formed. The reaction mixture was concentrated under reduced pressure to give a residue. The mixture was dissolved in EtOAc (20 mL), and then strried at 20 C for 5 mins. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give desired 5-bromothiophene-2-sulfonamide (1.5 g, crude) as a white solid. |
With ammonia; at 15℃; for 0.2h; | To a solution of 5-bromothiophene-2-sulfonyl chloride (2 g, 7.65 mmol, 1 eq) in ammonia (1.95 g, 115 mmol, 1.92 mL, 15 eq). The mixture was stirred at 15 C for 0.2 hour. TLC (petroleum ether/EtOAc = 3/1) indicated 5-bromothiophene-2-sulfonyl chloride was consumed completely and new spot formed. The reaction mixture was concentrated under reduced pressure to give a residue. The mixture was dissolved in EtOAc (20 mL), and then strried at 20 C for 5 mins. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give desired 5-bromothiophene-2-sulfonamide (1.5 g, crude) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; N,N-dimethyl-formamide; at 130 - 150℃; for 0.75h;Microwave irradiation; | INTERMEDIATE 29; This shows the preparation of 5-[(3-chlorophenyl)thio]thiophene-2-sulfonamide,To a solution of 3-chlorobenzenethiol (87 mg) and 5-bromothiophene-2-sulfonamide (121 mg) in DMF (1 mL) was added aqueous 2 N sodium hydroxide solution (100 μL) and water (1 mL). The reaction was heated in a CEM Discover microwave for 15 rain at 130 C, then for a further 30 min at 150 C. The dark solution was partitioned between diethyl ether and water, and the organic phase was dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by RPHPLC (Xterra, 5% to 95% acetonitrile in TFA (0.2% aq.)) to give the title compound 5-[(3- chlorophenyl)thio]thiophene-2-sulfonamide (35 mg).1H NMR (300 MHz, DMSO) δ 7.79 (s, 2H), 7.56 (d, 1H), 7.47 (d, 1H), 7.44 - 7.35 (m, 3H), 7.30 - 7.26 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃;Inert atmosphere; Sealed tube; | Preparative Example 24PREPARATION OF 5-(3,4-DIMETHOXYPHENYL)THIOPHENE-2-SULFONAMIDEA stirred solution of 5-bromothiophene-2-sulfonamide (2 g, 8.26 mmol) and (3,4-dimethoxyphenyl)boronic acid (1.8 g, 9.90 mmol) in 30 mL DMF at room temperature was purged with N2 gas for 10 mins. To this stirred solution was added (Ph3P)4Pd (1.9 g, 1.65 mmol) and saturated Na2CO3/H2O (2.63 g, 3 mmol). The N2 purge was stopped and the reaction mixture was sealed and heated with a preheated oil bath at 100 C. overnight. The reaction mixture was filtered and the filtrate was partitioned between saturated NaHCO3 and EtOAc, the layers were separated, and the aqueous layer was extracted again with EtOAc. The combined organic layers were dried (MgSO4), filtered, and evaporated in vacuo. The resulting material was purified by silica gel chromatography (40% EtOAc in hexane) to provide the product, as a light yellow solid.1H NMR (500 MHz, CD3OD) δ (ppm): 7.56 (d, 1H), 7.30 (d, 1H), 7.24 (m, 2H), 7.00 (d, 1H), 3.90 (d, 6H). | |
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 20 - 100℃;Sealed tube; | PREPARATIVE EXAMPLE 10 PREPARATION OF 5-(3,4-DIMETHOXYPHENYL)THTOPHENE-2-SULFON AMIDEA stirred solution of 5-bromothiophene-2-suIfonamide (2 g, 8.26 mmol) and (3,4- dimethoxyphenyl)boronic acid (1.8 g, 9.90 mmol) in 30 mL DMF at room temperature was purged with N2 gas for 10 mins. To this stirred solution was added (Ph3P)4Pd (1.9 g, 1.65 mmol) and saturated Na2CO3/H2θ (2.63 g, 3 mmol). The N2 purge was stopped and the reaction mixture was sealed and heated with a preheated oil bath at 1000C overnight. The reaction mixture was filtered and the filtrate was partitioned between saturated NaHCO3 and EtOAc, the layers were separated, and the aqueous layer was extracted again with EtOAc. The combined organic layers were dried (MgSO^), filtered, and evaporated in vacuo. The resulting material was purified by silica gel chromatography (40% EtOAc in hexane) to provide the product, as a light yellow solid.1H NMR (500 MHz, CD3OD) δ (ppm): 7.56 (d, IH), 7.30 (d, IH), 7.24 (m, 2H), 7.00 (d, IH), 3.90 (d,SH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; | A mixture of intermediate (9) (0.002 mol) and <strong>[53595-65-6]5-bromo-2-thiophenesulfonamide</strong> (0.0025 mol) in dioxane (40 ml) was degassed and a flow of nitrogen was brought over the reaction mixture (3 times). Then CS2CO3 (0.004 mol) was added and the mixture was degassed and nitrogen was brought over the reaction mixture again, (twice). Then Pd2(dba)3 (0.0001 mol) and Xantphos (0.0001 mol) were added and degassing and the nitrogen action were performed (twice). A nitrogen balloon was left on the reaction mixture and the mixture was stirred overnight at 1000C. The mixture was cooled, filtered and the filtrate was evaporated, yielding intermediate (25). | |
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane;Inert atmosphere; | Example A.8 Preparation of [0178] [0179] A mixture of intermediate (9) (0.002 mol) and <strong>[53595-65-6]5-bromo-2-thiophenesulfonamide</strong> (0.0025 mol) in dioxane (40 ml) was degassed and a flow of nitrogen was brought over the reaction mixture (3 times). Then Cs2CO3 (0.004 mol) was added and the mixture was degassed and nitrogen was brought over the reaction mixture again. (twice). Then Pd2(dba)3 (0.0001 mol) and Xantphos (0.0001 mol) were added and degassing and the nitrogen action were performed (twice). A nitrogen balloon was left on the reaction mixture and the mixture was stirred overnight at 100 C. The mixture was cooled, filtered and the filtrate was evaporated, yielding intermediate (25). |