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[ CAS No. 98-62-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 98-62-4
Chemical Structure| 98-62-4
Chemical Structure| 98-62-4
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Product Details of [ 98-62-4 ]

CAS No. :98-62-4 MDL No. :MFCD00007883
Formula : C6H6FNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :BPUKPIBWYZWYQV-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :66823
Synonyms :

Safety of [ 98-62-4 ]

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:
GHS Pictogram:

Application In Synthesis of [ 98-62-4 ]

* 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.

  • Downstream synthetic route of [ 98-62-4 ]

[ 98-62-4 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 98-62-4 ]
  • [ 124-41-4 ]
  • [ 55034-26-9 ]
YieldReaction ConditionsOperation in experiment
With methanol
  • 2
  • [ 349-96-2 ]
  • [ 98-62-4 ]
YieldReaction ConditionsOperation in experiment
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]'.
  • 3
  • [ 98-62-4 ]
  • [ 30880-64-9 ]
  • [ 30880-76-3 ]
YieldReaction ConditionsOperation in experiment
(i) SOCl2, (ii) /BRN= 2209488/; Multistep reaction;
  • 4
  • [ 98-62-4 ]
  • [ 21105-10-2 ]
  • 4-[2-(2-Chloro-4-nitro-phenoxy)-propionylamino]-benzenesulfonyl fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
(i) SOCl2, (ii) /BRN= 2209488/; Multistep reaction;
  • 5
  • [ 98-62-4 ]
  • [ 1878-88-2 ]
  • [ 30885-87-1 ]
  • 6
  • [ 98-62-4 ]
  • [ 30880-72-9 ]
  • 4-[3-(2-Chloro-4-nitro-phenoxymethyl)-benzoylamino]-benzenesulfonyl fluoride [ No CAS ]
  • 7
  • [ 98-62-4 ]
  • [ 30880-70-7 ]
  • 4-[4-(2-Chloro-4-nitro-phenoxymethyl)-benzoylamino]-benzenesulfonyl fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
(i) SOCl2, (ii) /BRN= 2209488/; Multistep reaction;
  • 8
  • [ 125-84-8 ]
  • [ 98-62-4 ]
  • [ 201336-47-2 ]
  • 9
  • [ 10350-07-9 ]
  • [ 98-62-4 ]
  • [ 220208-07-1 ]
  • 10
  • [ 98-62-4 ]
  • [ 144-80-9 ]
  • 4-(4-aminophenylsulfonamido)-sulfacetamide [ No CAS ]
  • 11
  • [ 98-62-4 ]
  • [ 109-85-3 ]
  • [ 328062-38-0 ]
YieldReaction ConditionsOperation in experiment
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]+.
  • 12
  • [ 98-62-4 ]
  • 4-(3-Allyl-thioureido)-N-phenoxathiin-2-yl-benzenesulfonamide [ No CAS ]
  • 13
  • [ 98-62-4 ]
  • 4-[3-(3,4-Dichloro-phenyl)-ureido]-N-phenoxathiin-2-yl-benzenesulfonamide [ No CAS ]
  • 14
  • [ 98-62-4 ]
  • N1-[4-(phenoxathiin-2-yl-aminosulfonyl)phenyl]-N3-tosyl-urea [ No CAS ]
  • 15
  • [ 98-62-4 ]
  • 2,4,6-Trimethyl-1-[4-(phenoxathiin-2-ylsulfamoyl)-phenyl]-pyridinium; perchlorate [ No CAS ]
  • 16
  • [ 98-62-4 ]
  • 2,6-Dimethyl-1-[4-(phenoxathiin-2-ylsulfamoyl)-phenyl]-4-phenyl-pyridinium; perchlorate [ No CAS ]
  • 17
  • [ 98-62-4 ]
  • 1-[4-(Phenoxathiin-2-ylsulfamoyl)-phenyl]-2,4,6-triphenyl-pyridinium; perchlorate [ No CAS ]
  • 18
  • [ 98-62-4 ]
  • 4-[3-(3,4-Dichloro-phenyl)-ureido]-N-[4-(3-ethyl-2,6-dioxo-piperidin-3-yl)-phenyl]-benzenesulfonamide [ No CAS ]
  • 19
  • [ 98-62-4 ]
  • 3-ethyl-3-{4-[4-(tosylsulfonylureido)phenylsulfamoyl]phenyl}-2,6-piperidinedione [ No CAS ]
  • 20
  • [ 98-62-4 ]
  • 1-{4-[4-(3-Ethyl-2,6-dioxo-piperidin-3-yl)-phenylsulfamoyl]-phenyl}-2,4,6-trimethyl-pyridinium; perchlorate [ No CAS ]
  • 21
  • [ 98-62-4 ]
  • [ 13991-78-1 ]
  • 22
  • [ 98-62-4 ]
  • N-(p-Fluorsulfonyl-phenyl)-β-(4-amino-2-chlor-phenyl)-propionsaeureamid [ No CAS ]
  • 23
  • [ 98-62-4 ]
  • (N-<4-Fluorsulfonyl>)-(2-chlor-4-amino-phenoxy)-acetamid [ No CAS ]
  • 24
  • [ 98-62-4 ]
  • p-Amino-α-(p-tolyl)-phenylpropionsaeure-p-fluorsulfonyl-anilid [ No CAS ]
  • 25
  • [ 244144-51-2 ]
  • [ 98-62-4 ]
  • R-N-[2-chloro-4-(4-fluorosulphonylanilinosulphonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 26
  • [ 254878-30-3 ]
  • [ 98-62-4 ]
  • [ 254878-45-0 ]
  • 27
  • [ 98-62-4 ]
  • [ 41994-44-9 ]
  • [ 254878-44-9 ]
  • 28
  • [ 463-71-8 ]
  • [ 98-62-4 ]
  • [ 500727-77-5 ]
YieldReaction ConditionsOperation 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.
  • 29
  • [ 98-62-4 ]
  • [ 74-89-5 ]
  • [ 1709-52-0 ]
YieldReaction ConditionsOperation 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.
  • 30
  • [ 7663-77-6 ]
  • [ 98-62-4 ]
  • [ 403792-74-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tert-butyl alcohol; for 10h;Heating / reflux; Sulphanilyl fluoride (6.5 g, 37.1 mmol), 3-(pyrrolidin-2-on-1-yl)propylamine (5.79 g, 40.8 mmol) and triethylamine (5.69 ml, 40.8 mmol) in n-butanol (15 ml) was heated at reflux for 10 hours. The mixture was allowed to cool, silica was added and the volatiles were evaporated. The residue was purified by chromatography eluding with DCM/MeOH- (100:0) increasing in polarity to (90:10) to give the title compound m/z: 297.
  • 31
  • [ 26734-09-8 ]
  • [ 98-62-4 ]
  • [ 222037-06-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In butan-1-ol; Method 4 4-[N-(3-hydroxy-2.2-dimethylpropyl)sulphamoyl]aniline A mixture of sulphanilyl fluoride (1g, 5.7 mmol), 3-amino-2,2-dimethylpropan-1-ol (884 mg, 8.6 mmol) and triethylamine (0.876 ml, 6.3 mmol) in butan-1-ol (20 ml) was heated at reflux for 24 hours. The volatiles were removed by evaporation and residue was purified by chromatography on silica gel to give the title compound. NMR: 0.72 (s, 6H), 2.52 (d, 2H), 3.08 (d, 2H), 4.40 (t, 1H), 7.19 (t, 1H), 7.60 (s, 1H), 7.64 (d, 2H), 7.96 (d, 2H), 8.40 (s, 1H), m/z 259 (MN)+.
  • 32
  • [ 389606-12-6 ]
  • [ 98-62-4 ]
  • [ 389606-53-5 ]
YieldReaction ConditionsOperation in experiment
93% In iso-butanol; Method 111 5-Cyano-4-ethylamino-2-[4-(fluorosulphonyl)anilino]pyrimidine 2-Chloro-5-cyano-4-ethylaminopyrimidine (Method 56; 6.35 g, 34.88 mmol) and sulphanilyl fluoride (6.11 g, 34.88 mmol) in 2-butanol (120 ml) were heated at 95 C. for 4 hours and then stirred at ambient temperatures for 48 hours. The volatiles were evaporated and the residue triturated with ether to give the title compound (10.46 g, 93%). NMR: 1.20 (t, 3H), 3.45 (m, 2H), 8.00 (d, 2H), 8.13 (d, 2H), 8.41 (s, 1H), 10.52 (s, 1H); m/z: 321.
  • 33
  • [ 3360-16-5 ]
  • [ 98-62-4 ]
  • [ 389605-68-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In butan-1-ol; Method 1 4-[N-(3-Isopropylaminopropyl)sulphamoyl]aniline. Sulphanilyl fluoride (6.5 g, 37.1 mmol), N-isopropyl-1,3-propanediamine (5.71 ml, 40.8 mmol) and triethylamine (5.69 ml, 40.8 mmol) in N-butanol (15 ml) was heated at reflux for 10 hours. The mixture was allowed to cool, silica was added and the volatiles were evaporated. The residue was purified by chromatography eluding with DCM/methanolic ammonia (100:0) increasing in polarity to (90:10) to give the title compound as a clear oil which crystallized on standing (8.81 g, 88%). NMR: 0.89 (d, 6H), 1.43 (m, 2H), 2.41 (t, 2H), 2.58 (m, 1H), 2.68 (t, 2H), 3.16 (s, 2H), 5.85 (s, 2H), 6.58 (d, 2H), 7.38 (d, 2H); m/z: 272.
  • 34
  • [ 374-35-6 ]
  • [ 98-62-4 ]
  • 3,3,3-trifluoro-H-[4-(fluorosulfonyl)phenyl]-2-hydroxy-2-methylpropanamide [ No CAS ]
  • [ 167156-15-2 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In N,N-dimethyl acetamide; The starting 3,3,3-trifluoro-H-[4-(fluorosulfonyl)phenyl]-2-hydroxy-2-methylpropanamide was prepared as follows. To a cooled (-20 C.) solution of α-trifluoromethyl lactic acid (2.0 g) in dry N,N-dimethylacetamide (15 ml) was added thionyl chloride (0.97 mL) dropwise over 10 minutes. The reaction mixture was stirred at -20 C. for 1 hour, warmed to 0 C. over 1 hour, then treated with sulfanilyl fluoride (2.22 g) in one portion and heated at 100 C. for 24 hours. After cooling to 22 C. the reaction mixture was diluted with water (150 ml) and extracted with ethyl acetate (3*35 ml). The combined organic extracts were washed with water, brine, dried and the solvent removed under reduced pressure. The crude product was purified by chromatography (13:1 CH2 Cl2:Et2 O) and recrystallized from methyl-t-butyl ether to give 3,3,3-trifluoro-N-[4-(fluorosulfonyl)phenyl]-2-hydroxy-2-methylpropanamide as colourless crystals, (1.7 g); mp 152-154 C.; MS: m/z=316(M+1); NMR (CDCl3): 1.78 (s,3), 3.51 (broad s), 7.86-7.89 (m, 2), 7.99-8.03 (m,2), 8.79 (broad s,1). Analysis for C10 H9 F4 NO4 S: Calculated: C, 38.10; H,2.88; N, 4.44; Found: C, 38.21; H, 2.97; N, 4.44.
  • 35
  • [ 98-62-4 ]
  • 2,6-dibromo-4-fluorosulphonylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bromine; In water; acetic acid; i) Preparation of 2,6-dibromo-4-fluorosulphonylaniline To a solution of <strong>[98-62-4]4-aminobenzenesulphonyl fluoride</strong> (10 parts) in acetic acid (100 parts), stirring at 0-5 C., was added gradually a solution of bromine (18 parts) in acetic acid (50 parts); keeping the temperature below 5 C. The temperature was allowed to warm to ambient and the mixture was stirred at this temperature for a further 1 hr. The reaction mass was drowned into water (500 parts), the product was isolated by filtration, washed with cold water and dried at 50 C. to yield; 2,6-dibromo-4-fluorosulphonylaniline (17.5 parts).
  • 36
  • [ 81-62-9 ]
  • [ 98-62-4 ]
  • [ 142-71-2 ]
  • [ 170865-67-5 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In 1,2-dichloro-benzene; EXAMPLE 24 Preparation of 1-amino-4-(N-(4-fluorosulphonyl)phenyl)aminoanthraquinone 1-Amino-4-bromoanthraquinone (3.3 parts), sodium acetate (5 parts), cupric acetate (0.5 parts) and sulphanilyl fluoride (4 parts) were stirred in o-dichlorobenzene (88 parts) at 190 C. for 30 hours. The solution was allowed to cool and filtered, the solid was washed with water several times to give 1-amino-4-(N-(4-fluorosulphonyl)phenyl)aminoanthraquinone.
  • 37
  • [ 98-62-4 ]
  • [ 7693-46-1 ]
  • [ 21975-94-0 ]
YieldReaction ConditionsOperation in experiment
In benzene; EXAMPLE 8 4-{m-{3-[p-(Fluorosulfonyl)phenyl]ureido}benzamido}-5-hydroxy-2,7-naphthalenedisulfonic acid, disodium salt A mixture of 18.0 g of sulfanilyl fluoride, 20.0 g of p-nitrophenyl chloroformate and 95 ml of benzene (dried by distillation) is refluxed and stirred for 5 hours (a precipitate appears at about 4 hours). The mixture is then cooled and filtered, the precipitate is washed with cold benzene and is recrystallized from methylene chloride to give 19.86 g of p-(fluorosulfonyl)carbanilic acid p-nitrophenyl ester.
In benzene; EXAMPLE 8 4-{m-{3-[p-(Fluorosulfonyl)phenyl]ureido}benzamido}-5-hydroxy-2,7-naphthalenedisulfonic acid, disodium salt A mixture of 18.0 g of sulfanilyl fluoride, 20.0 g of p-nitrophenyl chloroformate and 95 ml of benzene (dried by distillation) is refluxed and stirred for 5 hours (a precipitate appears at about 4 hours). The mixture is then cooled and filtered, the precipitate is washed with cold benzene and is recrystallized from methylene chloride to give 19.86 g of p-(fluorosulfonyl)carbanilic acid p-nitrophenyl ester.
  • 38
  • [ 98-62-4 ]
  • [ 7693-46-1 ]
  • 4-m-3-[p-(Fluorosulfonyl)phenyl]ureido benzamido-5-hydroxy-1-naphthalenesulfonic acid sodium salt [ No CAS ]
  • [ 21975-94-0 ]
YieldReaction ConditionsOperation in experiment
In benzene; EXAMPLE 4 4-m-3-[p-(Fluorosulfonyl)phenyl]ureido benzamido-5-hydroxy-1-naphthalenesulfonic acid sodium salt A mixture of 18.0 g of sulfanilyl fluoride, 20 g of p-nitrophenyl chloroformate, and 95 ml of redistilled benzene is stirred and refluxed for a 5 hour period. The resulting mixture is then cooled and filtered and the precipitate is washed with cold benzene. The product is then recrystallized from methylene chloride to give 17.17 g of p-(fluorosulfonyl)carbanilic acid p-nitrophenyl ester.
  • 39
  • [ 26411-22-3 ]
  • [ 98-62-4 ]
  • [ 1206536-01-7 ]
  • 40
  • [ 1206536-01-7 ]
  • C16H16N2O4 [ No CAS ]
  • [ 98-62-4 ]
  • 41
  • [ 98-62-4 ]
  • [ 31715-35-2 ]
  • 42
  • [ 98-62-4 ]
  • [ 1400890-51-8 ]
  • 43
  • [ 98-62-4 ]
  • [ 1400890-45-0 ]
  • 44
  • [ 98-62-4 ]
  • [ 1400890-48-3 ]
  • 45
  • [ 98-62-4 ]
  • [ 71989-26-9 ]
  • (S)-(9H-fluoren-9-yl)methyl tert-butyl (6-((4-(fluorosulfonyl)phenyl)amino)-6-oxohexane-1,5-diyl)dicarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
311 mg With pyridine; trichlorophosphate; at -16℃; for 2.5h;Inert atmosphere; 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 (90.6μL, 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): δ 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, α-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): δ 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): δ 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.
  • 46
  • [ 32315-10-9 ]
  • [ 98-62-4 ]
  • (S)-1-(4-aminopiperidin-1-yl)-2-methylbutan-1-one [ No CAS ]
  • (S)-4-(3-(1-(2-methylbutanoyl)piperidin-4-yl)ureido)benzenesulfonyl fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% 4-Arninobenzenesulfonyl fluoride (80 mg, 457 [mol, 1 .0 eq) and triethyl amine (50 mg, 495 jimol, 1 .1 cq) were dissolved in CH2CI2 (5 mL) with stirring at -78 C.Triphosgene (50 mg, 183 jimol, 0.37 eq) dissolved in CH2C12 (5 mL) was added dropwise at -78 C. The reactants were then warmed to 0 C and stirred for 30 minutes (mm.). Thereafter the reactants and reaction products were cooled to 0 C. (S,)- 1 -(4- aminopiperidin-1-yl)-2-rnethylbutan-1-one (92 mg, 548 tmol, 1.2 eq) and triethyl amine(50 mg, 495 imol, 1.1 eq) dissolved in CH2C12 (5 mL) were added slowly and the resulting reaction mixture was further stirred at room temperature for 12 hours (h). The reaction was then quenched with the addition of HCI solution (1M, 15 mL). An organic layer was collected from the reaction mixture and the remaining aqueous layer was further extracted with ethyl acetate (EtOAc) three times. The obtained organic layers were combined andwashed with saturated NaC1 solution. The washed organic layer was dried over anhydrousmagnesium sulfate and was concentrated under vacuum. The obtained product (3 5mg;20%) was eluted by flash chromatography with (EtOAc: Hexane/ 7:3). The product wasfurther purified by crystallization (MeOH with water). Yield 20 %. ‘H NMR (d6-DMSO,300 Mhz): 3 0.70-0.90 (m, 3H), 0.97 (t, J= 6Hz, 3H), 1.2-1.4 (in, 3H), 1.4-1.6 (m, 1H),1.7-1.9 (m, 2H), 2.7-2.9 (m, 2H), 3.17 (t, J= 12 Hz, 1H), 3.7-3.8 (n-i, 1H), 3.89 (d, J= 10.2 Hz, 1H), 4.22 (br, 1H), 6.56 (t, J= 7.5 Hz, 1H), 7.73 (d, J= 9 Hz, 2H), 7.96 (d, J= 9 Hz, 2H), 9.21 (d,J= 7.5 Hz, 1H); Melting point (C): 263.3-265.6 (264.5).
  • 47
  • [ 32315-10-9 ]
  • [ 98-62-4 ]
  • [ 103-71-9 ]
YieldReaction ConditionsOperation in experiment
7(C). 4-Isocyanatobenz.enesulfonyl fluoride. In a 10 mL flask, 128 mg (0.43 eq) of triphosgene (Caution: triphosgene is toxic, a well functional fume hood is necessary for this procedure) was dissolved in 1 mL DCM. Solution temperature was kept at about 0 C by an ice bath and protected by an Ar balloon. 175 mg ( l mmol) <strong>[98-62-4]4-aminobenzenesulfonyl fluoride</strong> was dissolved into 1 mL DCM and this solution was added into the flask slowly by syringe over 10 min, followed by 0.14 mL ( 1 eq) Et3N. After the addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. (0195) Reaction can be monitored by quenching the solution with methanol, then submitting the sample to LCMS. The solution was concentrated by rotary evaporation, and 4-isocyanato benzenesulfonyl fluoride was obtained as a yellow oil (mixed with Et^N/HCl salt). The isocyanate product can be used as it is, or dissolved in DCM then directly use for next steps. This intermediate is not stable at room temperature as a crude product. A rapid wash with 1M HC1, followed by saturated sodium chloride, and drying over sodium sulfate afforded a material that could be stored for up to one week;. 4-isocyanatobenzenesulfonyl fluoride was obtained as yellow solid.
  • 48
  • [ 6484-25-9 ]
  • [ 98-62-4 ]
  • 4-((2-phenylquinazolin-4-yl)amino)benzenesulfonyl fluoride [ No CAS ]
  • 49
  • [ 98-62-4 ]
  • 4-azidobenzenesulfonyl fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With tert.-butylnitrite; trimethylsilylazide; In acetonitrile; at 0 - 20℃; for 0.5h; To a solution of <strong>[98-62-4]4-aminobenzenesulfonyl fluoride</strong> (525 mg, 3.00mmol) in MeCN (10 mL) at 0 C was added tert-butyl nitrite (435 μL, 3.30 mmol) followed bytrimethylsilyl azide (540 μL, 4.5 mmol). The reaction was warmed to room temperature, stirred for 30min and then concentrated under reduced pressure. Purification by column chromatography (4% Et2Oin Petrol) yielded a white solid (559 mg, 93%).
  • 50
  • [ 98-62-4 ]
  • (4-(fluorosulfonyl)phenyl)iminosulfur oxydifluoride [ No CAS ]
  • 51
  • [ 98-62-4 ]
  • [ 27074-03-9 ]
  • C14H11FN4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
(1) Preparation of diazonium salt:In a three-necked flask equipped with a stirrer, mix 4-chlorosulfonylbenzeneacetamide (12.0 g), potassium fluoride (180 g) and 240 ml of water. Stir reflux for 3h. Place in ice bath to precipitate. Wash coolant using 40C pH 4-5 tap water. Collect sediment. Dissolve precipitate of 0.1 moles 4- fluorosulfonanilide in 35 ml of concentrated hydrochloric acid and 350.0 ml of water. Add 0.1 mol of sodium nitrite in -5C - 5C of calcium chloride in ice bath. After 4-5h of diazotization, add sodium acetate to adjust the pH to pH 5-6. Filter. Wash.(2) Coupling reaction:Add 0.1 mol diazonium salt into a solution containing 0.1mol of coupling component. Place 200mL water and 18mL of 37% hydrochloric acid in an ice bath. React for 5-6h then adjust the pH of diazonium solution to pH 5-6 by adding sodium acetate. Filter the precipitate of dye. Wash with water and dry. The dye was purified by crystallization from acetone to give the dye of formula (I-1).
  • 52
  • [ 98-62-4 ]
  • [ 28141-13-1 ]
  • C15H13FN4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Preparation method with the embodiment 1, the difference between the: change the diazotization reagent, the diazotization reaction temperature, diazo compounds with the diazotization reagent reaction amount of substance than, diazo salt with the coupling reagent reaction amount of substance than, the different disperse dyes such as shown in the table below.
  • 53
  • [ 24939-24-0 ]
  • [ 98-62-4 ]
  • 54
  • [ 98-62-4 ]
  • 4-(N-(4-methylpyridin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 55
  • [ 98-62-4 ]
  • C11H8F2N2O4S2 [ No CAS ]
  • 56
  • [ 98-62-4 ]
  • C12H11FN2O4S2 [ No CAS ]
  • 57
  • [ 98-62-4 ]
  • C11H12FN3O4S2 [ No CAS ]
  • 58
  • [ 98-62-4 ]
  • C12H11FN2O5S2 [ No CAS ]
  • 59
  • [ 98-62-4 ]
  • C10H10FN3O4S2 [ No CAS ]
  • 60
  • [ 98-62-4 ]
  • C11H13FN2O4S2 [ No CAS ]
  • 61
  • [ 98-62-4 ]
  • C12H14FN3O4S2 [ No CAS ]
  • 62
  • [ 98-62-4 ]
  • C11H15FN2O5S2 [ No CAS ]
  • 63
  • [ 98-62-4 ]
  • C11H9FN2O4S2 [ No CAS ]
  • 64
  • [ 98-62-4 ]
  • 4-(N-(2-(dimethylamino)pyrimidin-5-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 65
  • [ 98-62-4 ]
  • C12H11FN2O5S2 [ No CAS ]
  • 66
  • [ 98-62-4 ]
  • C11H11FN2O5S2 [ No CAS ]
  • 67
  • [ 98-62-4 ]
  • C13H14FN3O6S2 [ No CAS ]
  • 68
  • [ 98-62-4 ]
  • C10H9FN2O4S3 [ No CAS ]
  • 69
  • [ 98-62-4 ]
  • C9H7FN2O5S2 [ No CAS ]
  • 70
  • [ 98-62-4 ]
  • C10H10FN3O4S2 [ No CAS ]
  • 71
  • [ 98-62-4 ]
  • C9H8FN3O5S2 [ No CAS ]
  • 72
  • [ 98-62-4 ]
  • C8H6FN3O4S3 [ No CAS ]
  • 73
  • [ 98-62-4 ]
  • C11H11FN2O4S2 [ No CAS ]
  • 74
  • [ 98-62-4 ]
  • 4-(N-(3-carbamoyl-5-methyl-1H-pyrazol-4-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 75
  • [ 98-62-4 ]
  • 4-(N-(1-methyl-1H-pyrazol-4-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 76
  • [ 98-62-4 ]
  • 4-(N-(thiophen-3-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 77
  • [ 98-62-4 ]
  • methyl 3-(4-(fluorosulfonyl)phenylsulfonamido)-5-methyl-1H-pyrrole-2-carboxylate [ No CAS ]
  • 78
  • [ 98-62-4 ]
  • 4-(N-(6-bromopyridin-3-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 79
  • [ 98-62-4 ]
  • 4-(N-(pyridin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 80
  • [ 98-62-4 ]
  • 4-(N-(1-methyl-1H-1,2,4-triazol-5-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 81
  • [ 98-62-4 ]
  • methyl 2-(4-(fluorosulfonyl)phenylsulfonamido)-4-methylthiazole-5-carboxylate [ No CAS ]
  • 82
  • [ 98-62-4 ]
  • C11H9FN2O4S2 [ No CAS ]
  • 83
  • [ 98-62-4 ]
  • 4-(chlorosulfonyl)benzenesulfonyl fluoride [ No CAS ]
  • 84
  • [ 98-62-4 ]
  • 4-(N-phenylsulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 85
  • [ 98-62-4 ]
  • 4-(N-(pyrimidin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 86
  • [ 98-62-4 ]
  • 4-(N-(4-chloropyridin-2-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
  • 87
  • [ 98-62-4 ]
  • C11H14FNO5S2 [ No CAS ]
  • 88
  • [ 98-62-4 ]
  • C11H9FN2O5S2 [ No CAS ]
  • 89
  • [ 98-62-4 ]
  • C11H8ClFN2O4S2 [ No CAS ]
  • 90
  • [ 98-62-4 ]
  • C10H9FN2O5S2 [ No CAS ]
  • 91
  • [ 98-62-4 ]
  • C14H15FN2O5S2 [ No CAS ]
  • 92
  • [ 98-62-4 ]
  • C11H8BrFN2O4S2 [ No CAS ]
  • 93
  • [ 98-62-4 ]
  • 4-(N-(1-methyl-1H-1,2,4-triazol-3-yl)sulfamoyl)benzene-1-sulfonyl fluoride [ No CAS ]
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