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CAS No. : | 98-62-4 | MDL No. : | MFCD00007883 |
Formula : | C6H6FNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 175.18 g/mol | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 | UN#: | 3261 |
Hazard Statements: | H302-H312-H332-H314 | Packing Group: | Ⅱ |
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 |
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With methanol |
Yield | Reaction Conditions | Operation in experiment |
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80% | With hydrogenchloride; iron; In ethanol; water; at 90℃; for 1h; | To a solution of <strong>[349-96-2]4-nitrobenzenesulfonyl fluoride</strong> (1.03 g, 5.00 mmol)in ethanol (60 mL) and water (15 mL) was added conc. hydrochloric acid (3 mL) and iron fillings (1.396 g, 25.00 mmol). The suspension was heated to 90 C for 1 h, cooled and filtered through ashort pad of silica, washing with ethanol (100 mL). The solution was concentrated in vacuo and theresidue extracted between EtOAc (80 mL) and 1M NaOH(aq) (80 mL). The organic layer was driedover MgSO4 and concentrated in vacuo. Purification by column chromatography (20% EtOAc inPetrol) yielded an off white solid (702 mg, 80%). |
With palladium on carbon; hydrogen; acetic acid; In ethyl acetate; for 3h; | To a solution of compound 9a (200.0mg, 0.975mmol) in 10mL EtOAc/ AcOH (1:1) was added 20% Pd/C catalyst (40.0mg). The reaction mixture was stirred under H2 atmosphere for 3h. The reaction mixture was filtered through Celite and the filtrate was evaporated to dryness under vacuum. The residue was dissolved in EtOAc (40mL) and washed with 5% NaHCO3 (10mL×3), H2O (10mL×2) and brine (10mL). The organic layer was dried over Na2SO4, filtered, and evaporated under vacuum to afford the crude aniline derivative, which was used without further purification. To a solution of the above crude aniline derivative and Fmoc-Lys(Boc)-OH (435.5mg, 1.023mmol) in 3mL anhydrous pyridine cooled in an ice/salt bath (-16C) under argon, was added freshly distilled POCl3 (90.6muL, 0.9747mmol). The reaction mixture was stirred for 2.5h, and then diluted with EtOAc (40mL). The EtOAc solution was washed with 5% citric acid (10mL×3), water (10mL×2), and brine (10mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The desired product was purified with silica gel column chromatography eluted with hexane/EtOAc (65/35). Compound 10a was obtained as a white solid (311mg, 51%), mp 113-114C. Rf=0.5 (hexane/EtOAc=1/1). 1H NMR (400MHz, CDCl3): delta 9.32 (s, 1H, NH), 7.87 (d, J=8.4Hz, 2H, aromatic), 7.77 (d, J=8.8Hz, 2H, aromatic), 7.74 (d, J=7.6Hz, 2H, aromatic), 7.55 (d, J=7.1Hz, 2H, aromatic), 7.37 (m, 2H, aromatic), 7.26 (m, 2H, aromatic), 5.69 (s, 1H, NH), 4.72 (s, 1H, NH), 4.41 (d, J=6.8Hz, 2H), 4.30 (m, 1H, alpha-H), 4.19 (t, J=6.8Hz, 1H), 3.17 (m, 1H), 3.05 (m, 1H), 1.96 (m, 1H), 1.72 (m, 1H), 1.52 (m, 2H), 1.44 (m, 2H), 1.42 (s, 9H); 13C NMR (100MHz, CDCl3): delta 171.4 (C), 156.9 (C), 156.6 (C), 144.6 (C), 143.5 (C), 143.4 (C), 141.2(C), 129.7 (CH), 127.8 (CH), 127.1 (CH), 126.8 (d, J=24.3Hz, C), 124.9 (CH), 120.0 (CH), 119.5 (CH), 79.6 (C), 67.4 (CH2), 55.6(CH), 46.9 (CH), 39.1 (CH2), 31.1 (CH2), 29.2 (CH2), 28.4 (CH3), 22.2 (CH2); 19F NMR (376MHz, CDCl3): delta 65.83. IR (KBr): 3283, 2940, 1685, 1588, 1516, 1404, 1250, 1209, 1178cm-1. HRMS calcd for C32H36FN3O7SNa (M+Na)+ 648.2156, found 648.2136. | |
With iron; ammonium chloride; In ethanol; dichloromethane; water; | 7(B).4-Aminobenzenesulfonyl fluoride: In a 500ml flask, 4.05 g (19.8 mmol) of 4-Nitrobenzene-l-sulfonyl fluoride was dissolved into 200 mL EtOH/H20 (8:1) solution at room temperature.1.1 g (1 eq) NH4CI was added into the solution. The solution was stirred for 10 min, 5.5 gram (5 eq) iron powder was added in one portion. The reaction mixture was stirred at room temperature and open to air. TLC and GCMS were used to monitor reaction, which was directly filtered when complete by Biichner funnel. The filter cake was carefully washed with 100 mL EtOAc three times. The filtrate was concentrated by rotary evaporation, extracted and washed with 200 mL DCM three times. The DCM solution was dried over sodium sulfate and concentrated. The pure product was obtained as yellow oil. (2.6 gram, 78% yield). NMR (400 MHz, Chloroform-*/) delta 7.71 (d, J= 8.7 Hz, 2H), 6.86 -6.41 (m, 2H),4.53 (s, 2H); 1:,CNMR(101 MHz, CDCI3) delta 153.43, 130.89, 119.18(d,J = 23 Hz), 114.03; 19F NMR (376 MHz, CDC13) delta 67.51; EI-MS (m/z): 175 [M]'. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) SOCl2, (ii) /BRN= 2209488/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
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(i) SOCl2, (ii) /BRN= 2209488/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
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(i) SOCl2, (ii) /BRN= 2209488/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
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65% | With triethylamine; In butan-1-ol; for 18h;Heating / reflux; | Method 24 4-[N-(2-Methoxyethyl)sulphamoyl]aniline A mixture of 2-methoxyethylamine (859mg, 11.4mmol), sulphanilyl fluoride (1.0g, 5.71mmol), and triethylamine (1.72g, 22.9mmol) in n-butanol (15ml) was heated at reflux for 18 hours. The mixture was allowed to cool and the volatiles were removed by evaporation. The residue was purified by chromatography eluding with ethyl acetate / hexane (50:50) increasing in polarity to (70:30) to give the title compound (860mg, 65%). NMR: 2.78 (q, 2H), 3.15 (s, 3H), 3.25 (t, 2H), 5.87 (s, 2H), 6.58 (d, 2H), 7.10 (t, 1H), 7.40 (d, 2H); m/z: 231 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of R-N-(2-chloro-4-chlorosulphonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropananide (Method M) (3.46 g, 9.45 mmol) in DCM (200 ml) was added to a stirred solution of 4-fluorosulphonylaniline (1.99 g, 11.3 mmol) and pyridine (1.52 ml, 18.2 mmol) in DCM (50 ml). The resultant mixture was stirred at ambient temperature overnight, evaporated to dryness and the residue treated with 1M aqueous hydrochloric acid (50 ml). The aqueous solution was extracted with EtOAc, the EtOAc extracts were washed with brine, dried and evaporated. The residue was purified by column chromatography using 30% EtOAc in DCM to yield the title compound as a foam (4.56 g, 9.05 mmol). NMR: 1.6 (s, 3H), 7.45 (d, 2H), 7.9 (dd, 1H), 8.0 (d, 1H), 8.05 (d, 2H), 8.3 (d, 1H); MS: 504. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogenchloride; In water; for 0.5h; | First 4-isothiocyanato-benzenesulfonyl fluoride, which has the structural formula was prepared. According to a method from MCKEE et AL., J. Am. Chem. Soc. , 48 (1946), 2506-2507, sulfanilyl fluoride (6.00 g, 34.3 MMOL, from Sigma-Aldrich Chemical--discontinued ; see Krazer Helv. Chim. Acta. 43, 1513-1519 (1960) ) was dissolved in water (60 mL) containing 38% HCI (14.4 mL). Thiophosgene (2.7 mL, 36.0 MMOL) was added in one portion. The resultant mixture was stirred rapidly for a half hour, then diluted with water (200 mL). The resultant white precipitate was filtered off, washed with water, and dried under high vacuum to obtain 7.28 G (99%) of white powder, which was used without further purification. 1HNMR (DMSO-D6) : 8 8. 03 (2H, d, J = 9. 3 HZ), 7.44 (2H, d, J = 9. 3 HZ). FABMS: (M-H+) : 216. 2-Bromo-2', 6'-difluoroacetophenone, which has the structural formula was prepared as follows. To a mechanically stirring solution of 2', 6'-difluoroacetophenone (100.0 G, 640.0 mmol ; Melford Laboratories, Ltd. ) in ethyl acetate (1300 mL) were added freshly milled copper (II) bromide (300 G, 1.35 mol) and bromine (1.6 mL, 32 MMOL). The mixture was heated at reflux for 2.25 hours and allowed to cool to ambient temperature. The resultant green mixture was filtered and the solids rinsed with ethyl acetate (4x100 mL). The filtrate was concentrated with a rotary evaporator under reduced pressure, diluted with methyl t-butyl ether (MTBE; 650 mL), filtered through a pad of silica gel (230-400 ; 9.5 cm diam. X4 cm. ht. ), and solids rinsed with MTBE (5x200 mL). Concentration of the filtrate gave a pale green oil, which was purified by fractional vacuum distillation to give 117 g of pale yellow oil, bp 88-97C (2.0 mm Hg) in 78% yield. Matched that previously described in World Patent APPLICATION W099/21845 (in Example C (79) ) and was used without any further purification or characterization. 1H NMR: 8 7.48 (1H, ddd, J = 6.3, 8.5, 14.8 Hz), 7.01 (2H, ddd, J = 4.6, 5.8, 16.6 Hz), 4.37 (2H, t, J = 0. 7 HZ). 4- [4-AMINO-5- (2, 6-DIFLUORO-BENZOYL)-THIAZOL-2-YLAMINO]-BENZENESULFONYL FLUORIDE, which has the structural formula was then made as follows. To 4-isothiocyanato-benzenesulfonyl fluoride (4.00 G, 18.4 MMOL) and cyanamide (851 mg, 20.3 MMOL) in CH3CN (20 mL), in a vessel placed in a cold-water bath, was added 1,8- diazabicyclo [5.4. 0] undec-7-ene (DBU; 3.0 mL, 20 MMOL). After 15 minutes, a solution of 2- bromo-2', 6'-difluoro-acetophenone (4.54 g, 19.3 mmol ; from Example A (1)) in CH3CN (1 mL) and DBU (3.0 mL, 20. 3 MMOL) were sequentially added. The mixture was stirred at ambient temperature for a half-hour, then partitioned between CH2C12 and water, and acidified to pH=4 with 1 N HCI. The organic layer was separated, washed with brine, and dried over NA2SO4. The solvent was evaporated to give a hard foam, which was purified via column chromatography with 1: 1 ethyl acetate (EtOAc) and hexane (hex) as eluant to afford 6.2 G (82% yield) of a yellow powder. 1H NMR (DMSO-D6) : 8 11.50 (1 H, s), 8.35 (2H, bm), 8.10 (2H, d, J = 9.0 Hz), 7.96 (2H, d, J = 9. 0 HZ), 7.58 (1H, m), 7.24 (2H, dd, J = 7. 8,8. 2 HZ). Anal. calcd. for C16H10F2N3O3S2No.0. 1 EtOAc: C, 46.65 ; H, 2.58 ; N, 9.95 ; S, 15.19. Found: C, 46.65 ; H, 2 : 55 ; N, 9.80 ; S, 15.02. The title compound was prepared as follows. A mixture of 4- [4-AMINO-5- (2, 6-DIFLUORO- benzoyl)-thiazol-2-ylamino]-benzenesulfonyl fluoride (200 mg, 0.484 MMOL), piperazine (125 mg, 1.45 MMOL), CH3CN (2 mL), and 4- (N, N-dimethylamino)-pyridine (DMAP; 5 mg) was refluxed for 2 hours. The solvent was removed under reduced pressure, the residue was taken up into MeOH (2 mL), then precipitated with water, filtered, and washed with water. Further purification with column chromatography gave 91 mg (43% yield) of a yellow powder. 1H NMR (DMSO-D6) : 8 8.22 (2H, bs), 7.83 (2H, d, J = 8.7 Hz), 7.68 (2H, d, J = 8.7 Hz), 7.56 (1H, m), 7.22 (2H, dd, J = 7. 8,8. 2 HZ). HRESIMS : calcd. for C2OH2OF2N503S2 (M+H+) : 480.0976. Found: 480.0988. Anal. CALCD. for C2OHI9F2NS03S2 0. 7 MeOH : C, 49.53 ; H, 4.38 ; N, 13.95 ; S, 12.78. Found: C, 49.51 ; H, 4.39 ; N, 13.84 ; S, 12.93. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethylamine; In ethanol; at 20 - 80℃; for 24h; | Method 23 4-(N-Methylsulphamoyl)aniline Methylamine (3ml of a 33% solution in ethanol) and then triethylamine (0.159ml, 1.1mmol) was added to sulphanilyl fluoride (200mg, 1.1mmol), and the mixture heated at 80C for 6 hours then at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue azeotroped with toluene to give the title compound (160mg, 76%). NMR: 2.30 (s, 3H), 5.85 (s, 2H), 6.60 (d, 2H), 7.39 (d, 2H); m/z: 187 [MH]+. |
75% | In ethanol; at 20 - 80℃; | 4-Aminobenzenesulphonylfluoride (200 mg, 1.14 mmol) was dissolved in a solution of methylamine in EtOH (3 mL, excess) and heated to 80 C. for 45 minutes, then cooled to room temperature and left to stir overnight. The solvent was evaporated in vacuo and azeotroped with ether to yield the title compound as a solid (160 mg, 75%). NMR: 2.12 (s, 31), 5.85 (s, 2H), 6.59 (d, 2H), 7.37 (d, 2H); miz 187. |