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CAS No. : | 776-04-5 | MDL No. : | MFCD00051696 |
Formula : | C7H4ClF3O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZIZGWNOAHUCACM-UHFFFAOYSA-N |
M.W : | 244.62 | Pubchem ID : | 136616 |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
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 |
---|---|---|
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 |
---|---|---|
60% | With triethylamine; In dichloromethane; at 23℃; for 2.5h; | Example 1, 7V-(2,3-dihydro-lH-inden-2-yl)-2-(trifluoromethyl)benzenesulfonamide; [0156] A solution of 2-(trifluoromethyl)benzenesulfonyl chloride (d 1.585, 62 L, 0.40 mmol) and triethylamine (d 0.726, 0.25 mL, 1.6 mmol) in dichloromethane (4 mL) was treated with <strong>[2338-18-3]2-aminoindan hydrochloride</strong> (68 mg, 0.40 mmol) at 23 0C. After 2.5 hours, the reaction solution was washed with 1 N aqueous sodium hydroxide (4 mL), water (4 mL) and saturated brine (4 mL). The organic solution was dried (MgSO4) and concentrated under vacuum to provide a clear oil that was dissolved in dichloromethane and pre-adsorbed on silica gel (1 g). Flash column chromatography on an ISCO (4 g silica gel) eluting ethyl acetate-hexanes (0-30 % solution (at) 18 mL/min) provided N-(2,3-dihydro- lH-inden-2-yl)-2- (trifluoromethyl)benzenesulfonamide (82 mg, 60 %) as a white solid. MS (ES) m/z 341.7 ([M+eta]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In dichloromethane; at 20℃;Inert atmosphere; | Methyl 3-amino-4-fluorobenzoate (2 g, 13 mmol) and pyridine (2.1 g, 76.4 mmol) were suspended in DCM (25 mL), and to the stirring solution was slowly added 2-trifluoromethyl- benzenesulfonyl chloride (3.24 g, 13 mmol) at room temperature. After stirring for 2 h, the reaction mixture was washed with water and then extracted with DCM. The combined organic layers were dried over Na2SOzI, filtered, and concentrated in vacuo. The crude residue was suspended in water (30 mL) followed by slow addition of NaOH (1.1 g, 28 mmol), and the mixture heated at reflux overnight. After cooling to room temperature, the reaction mixture was extracted with DCM. The layers were separated. The aq. layer adjusted to pH 5 with aq. 5N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the final product as a solid (4.0 g, 83percent overall). LC-MS (ES) m/z = 364.1 (M+H)+ 1H NMR (400 MHz, DMSO-d6) delta ppm 10.61 (br, 1 H), 10.37 (br, 1 H), 8.78 (m, 1 H), 8.37 (m, 1 H), 8.01 (m, 2 H), 7.71 (m, 2 H), 7.31 (m, 2 H). |
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