There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 146949-07-7 | MDL No. : | MFCD00041508 |
Formula : | C9H11ClO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LEFGAGRZHLNPLS-UHFFFAOYSA-N |
M.W : | 218.70 | Pubchem ID : | 2737222 |
Synonyms : |
|
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 |
---|---|---|
With ammonium hydroxide at 40℃; for 0.5h; Yield given; | ||
With ammonia In acetone at 20℃; for 0.0333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; | General Method for Synthesis of arylsulphonamide (, STX576-577,. STX702. STX770); To a solution of amine (1 eq. ) in DMF was added Et3N (5 eq.), followed by corresponding sulphonyl chloride (1.2 eq. ). The reaction mixture was stirred at rt under N2 overnight, poured into water after TLC showed completion of the reaction, and extracted with ethyl acetate, dried (MgSO4), concentrated under reduced pressure to give the desired sulphonamide as crystalline solid or as a thick syrup. The crude compound was then purified by flash chromatography using EtOAc/hexane (3: 2) or CH2CI2/EtOAc (4: 1) as eluent to give crystalline solid. Yield 20-80%.; 4-Propvl-N-r1- (4-propvlbenzenesulfonvl)-piperidin-4-vlmethvll-benzenesulfonamide (STX576, DGS03094A); White solid. mp 158-159°C ; TLC single spot at Rf 0.59 (20% ethyl acetate-DCM); HPLC purity 99% (tR 2.0 min in 4% water-methanol) ;'H NMR (400 MHz, DMSO-d6): No. 7.60- 7.66 (4H, m, ArH), 7.55 (1H, broad, NH), 7.35-7. 45 (4H, m, ArH), 3.55-3. 58 (2H, dd, J = 7.2, 2.3 Hz, CH2), 2.56-2. 67 (6H, m, 3 x CH2), 2.04-2. 10 (2H, m, CH2), 1.54-1. 65 (6H, m, 3 x CH2), 1.23 (1H, m, CH), 1.02-1. 11 (2H, m, CH2), 0.85-0. 89 (6H, m, 2 x CH3) ; FAB- MS 479 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In dichloromethane; at 20 - 40℃; for 4 - 14h; | Synthesis of pyrazolyl arysulphonamides and benzopyrazole arysulphonamides; General Method for Synthesis of arylsulphonamide and N-arylsulphonyl arylsulphonamide (STX769, STX829-830, STX880-884); To a solution arylsulphonyl chloride (1.05 eq. ) in DCM were added pyridine (2.1 eq. ) and the amine (1 eq. ). The reaction mixture was stirred at rt or 40C under nitrogen for 4-14 h, then partitioned between ethyl acetate and 5% sodium bicarbonate solution after TLC showed completion of the reaction. The organic layer was washed with brine, dried over sodium sulphate, and concentrated in vacuo to give crude product that was separated by flash chromatography (ethyl acetate-DCM gradient elution) to give arylsulphonamide and N-arylsulphonyl arylsulphonamide as white or off-white solid (Yield 30-80%).; N- (2-N-ethvl-2H-pyrazol-3-vl)-N- (4-n-propvlphenvlsulphonyl)-4-n- propvlbenzenesulfonamide (STX769, XDS01152); White powder. TLC single spot at Rf 0.71 (10% ethyl acetate-DCM); HPLC purity 99% (tR 4.1 min in 10% water-methanol) ;'H NMR (400 MHz, DMSO-d6): # 7.62-7. 66 (4H, m, ArH), 7.56 (1H, d, J = 2.3 Hz, ArH), 7.47-7. 50 (4H, m, ArH), 5.93 (1H, d, J = 2.2 Hz, ArH), 3.66 (2H, q, J = 7.0 Hz, NCH2), 2.68 (4H, t J = 7.8 Hz, CH2) 1.63 (4H, m, 2 x CH2), 1.18 (3H, t, J = 7.0 Hz, CH3), 0.90 (6H, t, J = 7.6 Hz, 2 x CH3) ; FAB-MS 476 (MH+) ; FAB- HRMS calcd for C23H30N304S2 (MH+) 476.1678, found 476.1682 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.A N-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide 252A N-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide The title compound was prepared from 2-amino-4-(3-nitrophenyl)thiazole and 4-n-propylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a yellow solid (41.5 mg) with purity >90%: MS (pos) m/z 404.1, (neg) m/z 402.2; HRMS m/z 403.0062 (calc. of monoisotopic mass for C18H17N3O4S2 gives 403.0060). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
276A N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-4-propylbenzenesulfonamide The title compound was prepared from <strong>[21344-90-1]4-(2-chlorophenyl)-1,3-thiazol-2-amine</strong> and 4-n-propylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a white solid (30.9 mg) with purity >90percent. MS (pos) m/z 393.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
272A 4-Propyl-N-[4-(3-pyridinyl)-1,3-thiazol-2-yl]benzenesulfonamide The title compound was prepared from 4-(3-pyridyl)-1,3-thiazol-2-amine and 4-n-propylbenzenesulfonyl chloride as described in the synthetic METHOD B to give a white-yellow solid (2.3 mg) with purity >90%. MS (pos) m/z 360.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | General method for synthesis of adamantylmethyl arylsulphonamide derivatives:; To a solution of arylsulphonyl chloride (0.53 mmol, 1.06 eq.) in DCM (6 mL) was added pyridine (0.2 mL)5 followed by the corresponding amine (0.50 mmol, 1 eq.). The reaction mixture was stirred at ambient temperature under nitrogen overnight. PS-PS-trisamine (4.1 mmol/g5 100 mg) was added, the mixture was kept stirring for another 2h5 filtered and concentrated in vacuo to give the crude product that was purified by flash chromatography (Ethyl acetate-hexane gradient elution) to give desired arylsulphonamide as crystalline solid or amorphous solid.N-Adamantan-l-yImethyI-4-propyl-benzenesulfonamide (XDS03080, STX1368)The compound was prepared with general method. White crystals (102 mg5 59%) were obtained, mp 148-149 C; TLC single spot at Rf. 0.50 (20% ethyl acetate/hexane); 1H NMR (270 MHz5 CDCl3) delta 0.93 (3H, t, J= 7.2 Hz, CH3), 1.42 (6H5 d, J= 2.6 Hz5 3 x CH2), 1.54-1.70 (8H5 m, 4 x CH2), 1.95 (3H5 broad S5 3 x CH)5 2.57 (2H5 d, J= 6.7 Hz5 NCH2), 2.64 (2H, t, J= 7.2 Hz, CH2), 4.60 (IH5 1, J= 6.6 Hz, NH)5 7.29 (2H, m, ArH)5 and 7.73 (2H5 m5 ArH); HRMS (FAB+) calcd. for C20H30NO2S (M+-FH) 348.1997, found 348.2007; LC/MS (APCI) m/z 348 (M++..); HPLC tr = 3.29 min (>99%) in 10% water- acetonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | To a solution of 4n-propylbenzenesulphonyl chloride (163 mg, 0.744 MMOL) in dichloromethane (3 mL) was added pyridine (140 uL, 1.72 MMOL) and the mixture was stirred under N2 for 5 min, after which time 6-AMINO-2-METHYLBENZOXAZOLE (105 mg, 0.709 MMOL) was added. The resulting mixture was stirred for 1 h at room temperature, then saturated NAHC03 solution was added (8 mL) and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (NA2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a pale pink solid (164 mg, 70%), single spot at Rf 0.49 (60: 40 hexane: ethyl acetate). mp 101.7-102. 3C, HPLC purity 99% (tR 2.02 min in 10% water-acetonitrile). 'H NMR (CDCI3) : 6 7.61 (2H, m), 7.43 (1H, d, J=8.4 Hz), 7.37 (1H, d, J=1. 8 Hz), 7.19 (2H, m), 6.83 (2H, m), 2.57 (5H, m), 1.58 (2H, sextet, J=7.3 Hz), 0.88 (3H, t, J=7.3 Hz). LCMS: 329.21 (M-). FAB-MS (MH+, C17H18N203S) : calcd 331.1116, found 331.1107. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: 4-n-propylbenzenesulfonyl chloride With pyridine In dichloromethane for 0.0833333h; Stage #2: 2-methylquinolin-6-amine In dichloromethane at 20℃; for 1h; | Synthesis of N- (2-methvl-quinolin-6-yl)-4-propvl-benzenesulfonamide, STX 936 (KRB01062) :; To a solution of 4n-propylbenzenesulphonyl chloride (145 mg, 0.664 mmol) in dichloromethane (4 mL) was added pyridine (130 JL, 1.58 mmol) and the mixture was stirred under N2 for 5 min, after which time 6-amino-2-methylquinoline (100 mg, 0.632 mmol) was added. The resulting mixture was stirred for 1 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford an off-white solid (186 mg, 86%), single spot at Rf 0.70 (ethyl acetate). mp 173.7-174. 0°C, HPLC purity 99+% (tR 2.32 min in 10% water-acetonitrile).'H NMR (CDCI3) : 5 7.94 (1 H, d, J=8.4 Hz), 7.89 (1H, d, J=9.2 Hz), 7.67 (2H, d, J=8.4 Hz), 7.54 (1H, d, J=2.5 Hz), 7.31 (1H, dd, J=8.9, 2.5 Hz), 7.25 (1H, d, J=8.4 Hz), 7.19 (2H, d, J=8.4 Hz), 7.07 (1H, s, N- H), 2.70 (3H, s), 2.56 (2H, t, J=7.5 Hz), 1.58 (2H, sextet, J=7.4 Hz), 0.87 (3H, t, J=7.4 Hz). LCMS: 339.24 (M-). FAB-MS (MH+, C1gH20N202S) calcd 341.1323, found 341.1324. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Synthesis of 4-propyl-N-quinolin-6-vl-benzenesulfonamide, STX 933 (KRB01059) :; To a solution of 4n-propylbenzenesulphonyl chloride (159 mg, 0.728 mmol) in dichloromethane (4 mL) was added pyridine (140 uL, 1.74 mmol) and the mixture was stirred under N2 for 5 min, after which time <strong>[580-15-4]6-aminoquinoline</strong> (100 mg, 0.694 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (210 mg, 93%), single spot at Rf 0.71 (ethyl acetate). mp 180.1-180. 7C, HPLC purity 99+% (tR 2.37 min in 10% water-acetonitrile).'H NMR (CDC13) : 5 8.83 (1H, dd, J=4.2, 1.7 Hz), 8.05 (1H, d, J=8.4 Hz), 7.97 (1H, d, J=9.2 Hz), 7.70 (2H, d, J=8.2 Hz), 7.57 (1H, d, J=2.5 Hz), 7.40-7. 34 (2H, m), 7.22 (2H, m), 6.85 (1H, s, N-H), 2.57 (2H, t, J=7.2 Hz), 1.57 (2H, sextet, J=7.2 Hz), 0.87 (3H, t, J=7.3 Hz). LCMS: 325.23 (M- ). FAB-MS (MH+, C18H18N2O2S) : calcd 327.1167, found 327.1167. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Synthesis of N-(3-methyl-benzo[d]isozazol-5-yl)-4-propyl- benzenesulfonamide, STX875 (KRB01028) :; To a solution of 4n-propylbenzenesulphonyl chloride (124 mg, 0.567 mmol) in dichloromethane (3 rnL) was added pyridine (110 pL, 1.35 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-3-methyl-1, 2-benzisoxazole (80 mg, 0.54 mmol) was added. The resulting mixture was stirred for 3 h at room temperature, then saturated NaHCO3 solution (8 mL) was added and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a pale pink solid (150 mg, 84%), single spot at Rf 0.62 (1: 1 hexane: ethyl acetate). mp 119.5-120. 0C, HPLC purity 99+% (tR 2.29 min in 10% water-acetonitrile). 1H NMR (CDCI3) : No. 7.57 (2H, d, J=8.4 Hz), 7.40 (1H, d, J=2.2 Hz), 7.37 (1H, d, J=8.8 Hz), 7.20 (2H, d, J=8.4 Hz), 7.10 (1H, dd, J=8.8, 2.2 Hz), 6.71 (1H, s, N-/d), 2.59 (2H, t, J=7.5 Hz), 2.51 (3H, s), 1.59 (2H, sextet, J= 7.5 Hz), 0.88 (3H, t, J=7.5 Hz). LCMS: 314.07 (M- CH3). FAB-MS (MH+, Ci7HisN203S) : calcd 331.1116, found 331.1117 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | Synthesis of N-benzofdlisoxazol-5-yl-4-propyl-benzenesulfonamide, STX 919 (KRB01047) :; To a solution of 4n-propylbenzenesulphonyl chloride (171 mg, 0.783 mmol) in dichloromethane (4 mL) was added pyridine (150 uL, 1.86 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-1, 2-benzisoxazole (100 mg, 0.746 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (170 mg, 72%), single spot at Rf 0.68 (1: 1 hexane: ethyl acetate). mp 130.0- 130. 6C, HPLC purity 99+% (tR 2.44 min in 10% water-acetonitrile).'H NMR (CDCI3) : No. 8.62 (1H, d, J=1.0 Hz), 7.60 (2H, d, J=8.4 Hz), 7.48 (2H, m), 7.19 (3H, m), 6.86 (1H, s, N-H), 2.58 (2H, t, J=7.5 Hz), 1.58 (2H, sextet, J=7.4 Hz), 0.88 (3H, t, J=7.4 Hz). LCMS: 315.14 (M-). FAB-MS (MH+, deHOsS) : calcd 317.0960, found 317.0962 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Synthesis of 4-propvl-N-quinoxalin-6-vl-benzenesulfonamide, STX 958 (KRB01085) :; To a solution of 4n-propylbenzenesulphonyl chloride (142 mg, 0.651 mmol) in dichloromethane (4 mL) was added pyridine (125 uL, 1.55 mmol) and the mixture was stirred under N2 for 5 min, after which time <strong>[6298-37-9]6-aminoquinoxaline</strong> (90 mg, 0.62 mmol) was added. The resulting mixture was stirred for 4 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford an off-white solid (190 mg, 94%), single spot at Rf 0.66 (ethyl acetate). mp 198. 4-198. 9C, HPLC purity 99+% (tR 2. 22 min in 10% water-acetonitrile).'H NMR (CDCI3) : 68. 77 (1H, d, J=1.7 Hz), 8.73 (1H, d, J=1.7 Hz), 8.00 (1H, d, J=8.9 Hz), 7.80 (2H, d, J=8.2 Hz), 7.71 (1 H, d, J=2.5 Hz), 7.59 (1H, dd, J=8.9, 2.5 Hz), 7.23 (2H, obscured under CHCl3), 2.57 (2H, t, J=7.6 Hz), 1.58 (2H, sextet, J=7.5 Hz), 0.87 (3H, t, J=7.4 Hz). LCMS: 326.24 (M- ). FAB-MS (MH+, C17H17N302S) : calcd 328.1119, found 328.1136. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine In tetrahydrofuran at 20℃; for 12h; | General procedure for the synthesis of piroxicamderivatives (I-VI) General procedure: Synthetic scheme for the preparation of piroxicam derivativesis illustrated in the Scheme 1. Analogues were preparedby dissolving piroxicam with alkyl/aryl sulfonylchloride and TEA in THF, in a round bottom flask, withconstant stirring, without heating (Jayaselli et al., 2008).The end of reaction was monitored from TLC status, indifferent combination of ethyl acetate (EA) and n-hexane(Hex). The reaction completed in 8-12 h and the resultingproducts (Table 1) were filtered, washed with hot n-hexaneand excess of solvent was removed through vacuum underreduced pressure. Purity (95-100 %) of newly synthesizedderivatives was ascertained by TLC. Different spectroscopicprocedures like 1H-NMR, 13C-NMR, EIMS, IR, UVand CHN analysis were used for structural elucidation ofpiroxicam derivatives. (2-methyl-1,1-dioxide-3-(pyridine-2-ylcarbamoyl)-2H-benzo[e][1,2]thiazin-4-yl,4 propylbenzenesulfonate) (I) Yellowish-white powder (CHCl3): This compound was preparedby refluxing piroxicam (1 mmol) with npropylbenzenesulfonylchloride (1.6 mmol) and TEA(1 mmol) in THF (15 ml) as solvent, in round bottom flask,at room temperature for 12 h and product was obtained as ayellowish-white solid in a yield of 0.46 g (87 %); MP:164-175 °C; Rf: 0.62 (EA/Hex, 3:7); 1H-NMR: (C2H6OS,300 MHz): δH 10.92 (1H, s, NH), 8.36 (1H, d, J = 4.5 Hz,H-60), 7.84 (3H, m, H-5/8/30), 7.73 (3H, m, H-6/7/40), 7.56(2H, d, J = 8.4 Hz, H-200/600), 7.20 (3H, m, H-50/300H-500),3.02 (3H, s, NCH3), 2.50 (2H, t, CH2), 1.50 (2H, m, CH2),0.83 (3H, t, CH3); 13C-NMR (C2H6OS, 300 MHz):δC = 156.8 (C=Oamid.), 148.0 (C, C-3), 150.1 (C, C-4),127.4 (C, C-5), 114.1 (CH, C-6), 132.3 (CH, C-7), 120.4(CH, C-8), 125.4 (CH, C-9), 124.1 (C, C-10), 34.1 (CH3,C-11), 150.4 (C, C-20), 114.1 (CH, C-30), 138.2 (CH, C-40),120.4 (CH, C-50), 148.0 (CH, C-60), 150.8 (C, C-100), 129.7(CH, C-200), 128.2 (CH, C-300), 129.4, (C, C-400), 128.2 (CH,C-500), 129.1 (CH, C-600), 36.8 (CH2, C-700), 23.4 (CH2,C-800), 13.3 (CH3, C-900); IR (KBr) νmax: 3322, 2963, 2937,2872, 1690, 1516, 1433, 1357, 1299, 1181 cm-1; UV(CH2Cl2) λmax (log e): 201 (1.89), 230 (3.36), 312 (2.4) nm;EIMS m/z: (rel. abund. %), (M?, absent), 328 (3.5), 248(100), 220 (52), 122 (36.8), 44 (7); Anal. Calcd. for C24-H23N3O6S2: C, 56.13; H, 4.51; N, 8.18. Found: C, 56.11; H,4.48; N, 8.16. |
With triethylamine In tetrahydrofuran at 20℃; | 2.2. General procedure for the synthesis for synthesis of piroxicam derivatives (1-19) General procedure: Sulfonate esters of piroxicam were synthesized by dissolving piroxicam (1 mmol), alkyl/aryl sulfonyl chloride (1.2 mmol) and tri- ethylamine (1.2-1.8 mmol) in tetrahydrofurane (15 mL), in a round bottom flask via continuous stirring at room temperature ( Fig. 1 ) [1] . Resultant solid products (except of compound 4) were filtered and excess of solvent was removed through vacuum under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In tetrahydrofuran at 20℃; for 4h; | 37 General experimental procedures for the syntheses of coumarin sulfonates 4-43 General procedure: Coumarin sulfonates derivatives 4-43 were synthesized byreacting 3-hydroxy coumarin 1, 4-hydroxy coumarin 2 and 6-hydroxy coumarin 3 derivatives (1 mmol) with commercially available sulfonyl chlorides derivatives (1.2 mmol) in THF(15 mL) in the presence of triethyl amine (1 mmol). Reaction mixture was stirred for 4 h at room temperature to afford coumarin sulfonates 4-43. TLC monitoring was used to determine the progressof the reaction. After the completion of reaction, THF was evaporated and then solid product was washed with distilled water and dried under vacuum. The products were crystallized from methanol afforded good yields (Scheme 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine; In tetrahydrofuran; at 20℃; for 4h; | General procedure: Coumarin sulfonates 1-38 were synthesized by reactingdifferent hydroxylated coumarin derivatives (1 mmol) withcommercially available sulfonyl chlorides derivatives (1.2 mmol) inTHF (15 mL) and triethyl amine (1 mmol) was used as base. Reactionmixture was stirred for 4 h at room temperature to afford avariety of coumarin sulfonate esters 1e38. TLC monitoring wasused to determine the progress of the reaction. After the completionof reaction, THF was evaporated under reduced pressure andthe solid product obtained was washed with distilled water anddried under vacuum. The products were recrystallized in methanoland gave good yields. All the synthetic compounds 1-38 werecharacterized by different spectroscopic techniques such as EI-MS,HREI-MS, 1H-NMR, and 13C-NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine In tetrahydrofuran at 20℃; for 4h; | 4.2. General procedure for the synthesis of coumarin sulfonates(1-38) General procedure: Coumarin sulfonates 1-38 were synthesized by reactingdifferent hydroxylated coumarin derivatives (1 mmol) withcommercially available sulfonyl chlorides derivatives (1.2 mmol) inTHF (15 mL) and triethyl amine (1 mmol) was used as base. Reactionmixture was stirred for 4 h at room temperature to afford avariety of coumarin sulfonate esters 1e38. TLC monitoring wasused to determine the progress of the reaction. After the completionof reaction, THF was evaporated under reduced pressure andthe solid product obtained was washed with distilled water anddried under vacuum. The products were recrystallized in methanoland gave good yields. All the synthetic compounds 1-38 werecharacterized by different spectroscopic techniques such as EI-MS,HREI-MS, 1H-NMR, and 13C-NMR. |
With triethylamine In tetrahydrofuran at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 25h; | General procedure: <strong>[3366-95-8]Secnidazole</strong> (1 mmol) was dissolved in dioxane (6 mL) on icebath.After complete dissolution, we slowly added substitutedsulphonylchloride (1a-9a) (2 mmol). After 30 min, 33% aqueousNaOH (aq) solution (5 mL) was added to the reaction mixture withcontinuous stirring for 1 h. The ice bath was removed and stirringcontinued for 24 h at room temperature then reaction mixture waspoured onto ice-water, precipitates were obtained and recrystallizedwith minimum diethyl ether to obtain pure products (M1-M9). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
121 mg | Stage #1: 4-n-propylbenzenesulfonyl chloride; 4-chloro-2,5-dimethoxy-aniline With triethylamine In dichloromethane at 20℃; Stage #2: With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine at 20℃; for 2h; |