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CAS No. : | 1869-24-5 | MDL No. : | MFCD00042420 |
Formula : | C7H6F3NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AFFPZJFLSDVZBV-UHFFFAOYSA-N |
M.W : | 225.19 | Pubchem ID : | 2778018 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
83.7% | Synthesis Example 5 Synthesis of N-[(2-Trifluoromethylphenyl)sulfonyl]-5-methoxy-2-pyridinecarboxamide [Compound (I-54)] Using <strong>[1869-24-5]2-trifluoromethylbenzenesulfonamide</strong> [Compound (III-1)] (0.197 g, 0.87 mmol) and 5-methoxypicolinic acid phenyl ester [Compound (IV-54)] (0.2 g, 0.87 mmol), the Compound (I-54) was synthesised according to the process of Synthesis Example 1. White solid, yield: 0.262 g, percent yield: 83.7%, m.p.: 153-156 C. IR KBr cm-1: 3340, 1722, 1587, 1422, 1398, 1359, 1311, 1272, 1188, 1149, 588, 561. 1H-NMR (60 MHz, CDCl3, delta): 3.80 (3H, s, OCH3), 7.16 (1H, dd, J=3 Hz, 9 Hz, pyridine ring H), 7.46-7.80 (3H, m, aromatic ring H), 7.9 (1H, d, J=9 Hz, pyridine ring H), 8.13 (1H, d, J=3 Hz, pyridine ring H), 8.23-8.66 (1H, m, aromatic ring H), NH indistinctness. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.6% | Synthesis Example 27 Synthesis of 2-Trifluoromethylbenzenesulfonamide [Compound (III-1)] Using 2-trifluoromethylbenzenesulfonyl chloride [Compound (XXII-1)] (5 g, 0.0204 mol), the Compound (III-1) was synthesised according to the process of Synthesis Example 26. White solid, m.p.: 186-187 C., yield: 4.4 g, percent yield: 95.6%. IR KBr cm-1: 3394, 3274, 1347, 1161, 1140. 1H-NMR (60 MHz, d6-DMSO, delta): 7.4-7.9 (5H, m, aromatic ring H*3, NH2), 7.9-8.4 (1H, m, aromatic ring H). | |
89% | Intermediate 1 : 2-(trifluoiOmethyl)benzenesulfonamide (cf. Scheme 3, compound XXI)To a solution of 2-(trifluoromethyl)benzenesulfonyl chloride (5g; 20.44 mmol; 1.00 eq.) in anhydrous THF (5.00 ml) was added a solution of 71 ml Ammonia in Ethanol 2M under nitrogen at room temperature. The reaction mixture was shaken for 2Oh at room temperature. The solvent was evaporated and the residue redissolved in EtOAc(15OmL) and then washed with NH4Cl saturated aqueous solution (5OmL) and brine (5OmL). The organic layer was dried over MgSO4, filtered and the solvent evaporated to give the pure 2- (trifluoromethyl)benzenesulfonamide as a yellowish solid (4.6g, 89% yield, 98.6% HPLC purity). This compound was utilized as such for the next reaction.IH NMR (300MHz, CDCl3); 5.0 (m, 2H), 7.6 (m, 2H), 7.8 (m, IH), 8.3 (m, IH). MS(ESr): 224.1. | |
With ammonium hydroxide; In acetonitrile; at 0 - 20℃; for 1h;Inert atmosphere; | General procedure: In a 50 ml RB flask, sulfonyl chloride (500 mg) was taken in acetonitrile (5 ml) and the solution was cooled to 0 deg. Cel. To this aqueous ammonia solution (1.5 ml) was added dropwise. RM was then stirred at RT for 1 hr. RM was evaporated to dryness and the residue was then trichirated with minimum water and suspension was filtered and solid was dried to get the sulfonamide as solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; water; acetonitrile; | STR30 (by process (b)) At 20 C., 28.1 g (0.125 mol) of <strong>[1869-24-5]2-trifluoromethyl-benzenesulphonamide</strong> and a solution of 19 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) in 50 ml of acetonitrile are added in succession to a solution of 28.1 g (0.10 mol) of 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 300 ml of acetonitrile. The reaction mixture is stirred at 20 C. until a clear solution is obtained. The solution is then concentrated under water pump vacuum and the residue is admixed with water and methylene chloride (300 ml each) and acidified with 2N hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted once more with 100 ml of methylene chloride and the combined organic phases are dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum and the residue is crystallized from isopropanol. 29.6 g (72% of theory) of 4-methyl-5-methylthio-2-(2-trifluoromethyl-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 154 C. are obtained. By the methods of Examples 1, 2 and 3 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table 1 below. STR31 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In acetonitrile; at 20℃; for 24h; | General procedure: To a stirred solution of 3I-3III (10 mmol) and Et3N (12 mmol) in anhydrous acetonitrile was added sulfamide (4a-i and 5, 10 mmol) followed by addition EDCI (12 mmol) and DMAP (12 mmol). The mixture was stirred at r.t. for 24 h. The reaction mixture was concentrated, and the residue was dissolved in dichloromethane. The organic layer was washed with 1N HCl and water for 3 times respectively, dried over anhydrous Na2SO4 and evaporated in vacuum. The residue was subjected to silica gel chromatography or crystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [bis(acetoxy)iodo]benzene; sodium acetate; In dichloromethane; at 20℃; for 48h;Inert atmosphere; Schlenk technique; | General procedure: A Schlenk tube with a magnetic stir bar was charged with [RhCp*Cl2]2 (7.8 mg, 12.5 mumol), AgSbF6 (17.2 mg, 50 mumol), PhI(OAc)2 (120.4 mg, 0.375 mmol), NaOAc (6.2mg, 75 mumol), 8-methylquinoline derivative 1 (0.50 mmol), amide 2 (0.25 mmol), and DCM (1.0 mL) under an N2 atmosphere. The resulting mixture was stirred at room temperature for 48 h and then diluted with 3 mL of dichloromethane. The solution was filtered through a celite pad and washed with 10-20 mL of dichloromethane. The filtrate was concentrated and the residue was purified by column chromatography on silica gel to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | General procedure: All solid chemicals used were dried in vacuum over P2O5 overnight.The acid derivative and CDI were dissolved in dry THF underN2 atmosphere and the mixture was allowed to stir at 66-68 C for2 h. The sulfonamide and DBU dissolved in THF were added to thereaction mixture and stirring was continued at room temperature(4 h-overnight).Method B1: The solvent was removed in vacuo, water was addedand pH was adjusted to 2 by addition of 1 M HCl aq. The aqueousphase was extracted with EtOAc (2 40 ml), dried with MgSO4, filteredand evaporated in vacuo. For most of the compounds, a silicagel column was first run, followed by purification on aluminumoxide. |
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