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CAS No. : | 35303-76-5 | MDL No. : | MFCD00010301 |
Formula : | C8H12N2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FXNSVEQMUYPYJS-UHFFFAOYSA-N |
M.W : | 200.26 | Pubchem ID : | 169682 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 | UN#: | 3259 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
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 pyridine; sodium acetate; In water; acetone; benzene; | (a) 4-(beta-N'-2-quinolyl-N'-methylureidoethyl)-benzene-sulfonamide 76.5 Grams of <strong>[52430-43-0]2-methylaminoquinoline</strong> were mixed in 600 ml of absolute benzene with 39.5 g of pyridine and, while cooling with ice and stirring, treated with 49 g of phosgene. Stirring was continued for 1 hour, the salt precipitated was suction-filtered and washed well with benzene. The filtrate was evaporated, the residue taken up in 100 ml of acetone and added dropwise, while stirring and cooling with ice, to a mixture which contained in 290 ml of water 0.36 mol of 4-(beta-aminoethyl)-benzenesulfonamide and 0.72 mol of sodium acetate and was mixed with 290 ml of acetone. Stirring was continued for about 1 hour, the mixture was mixed with water, suction-filtered and recrystallized from ethanol - dimethylformamide. The reaction product obtained melted at 185-187 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere; | General procedure: Reactions of (1R)-(-)-10-camphorsulfonyl chloride 1 and (1S)-(+)-10-camphorsulfonyl chloride 2 (0.3 g,1.0 equiv) with amino derivatives 3 - 7 (1.0 equiv) were carried out at 0 C to room temperature in Schotten-Baumann conditions under nitrogen atmosphere, in the presence of a stoichiometric amount of dropwised dry TEA (1.0 equiv for 3, 5, 6 and 2.0 equiv for 4, 7), in dry DMF as solvent (2 ml). When complete (monitoring by TLC), reactions were quenched with crushed ice, extracted with ethyl acetate (20 ml), washed with 1 N HCl (2 x 10 ml) and brine (2 x 10 ml). The collected organic phase was dried on anhydrous Na2SO4, filtered and evaporated under vacuum. The crude was purified by silica gel column chromatography eluting with n-hexane/ethyl acetate or DCM/methanol to afford compounds 8-17 as white solids in medium yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium acetate; acetic anhydride; acetic acid; for 12h;Reflux; | General procedure: A mixture of 4-(2-aminoethyl)benzenesulfonamide (0.5 g,2.5 mmol), anhydrous sodium acetate (0.41 g, 5.0 mmol) and anacid anhydride (2.5 mmol) was stirred in glacial acetic acid(15 mL). The mixture was heated under reflux for 12 h and thereaction was monitored with the help of TLC. After completion ofreaction the solvent was removed under reduced pressure andthe crude solid obtained was washed with water, dried and recrystallisedfrom an appropriate solvent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In tetrahydrofuran; at 20℃; | 3-Ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate(1; 1.349 g, 5.5 mmol) and 4-(2-aminoethyl)benzenesulfonamide(1.001 g, 5 mmol) were dissolved in THF (40 mL), and themixture was stirred at r.t. over night. After completion of thereaction (TLC), the solvent was evaporated under reduced pressure,and the crude product was purified by crystallization(EtOAc) to give a white solid yield: 1.495 g, (85%); mp 183-185 C.1H NMR (400 MHz, DMSO-d6): delta = 8.37 (t, J = 5.2 Hz, 1 H), 7.45(d, J = 7.8 Hz, 2 H), 7.43 (d, J = 7.8 Hz, 2 H), 7.32 (s, 2 H), 4.17 (s, 2H), 3.49 (q, J = 6.0 Hz, 2 H), 2.88 (t, J = 6.5 Hz, 2 H), 2.18 (q, J = 7.3Hz, 2 H), 2.01 (s, 3 H), 0.97 (t, J = 7.4 Hz, 3 H). 13C NMR (100MHz, DMSO-d6): delta = 172.3, 152.5, 152.1, 143.8, 142.6, 132.3,129.5, 126.2, 52.3, 40.6, 35.5, 16.4, 13.3, 13.2. HRMS (ESI): m/z[M + Na]+ calcd for C16H21N3NaO4S: 374.1150; found: 374.1140. |
85.5% | In isopropyl alcohol; for 6h;Reflux; | The compound Kappa 5.0g, 4-(2-aminoethyl)benzenesulfonamide 4.08g and isopropanol 50g were heated under reflux for 6 h (4-(2-aminoethyl)benzenesulfonamide remaining 0.79%), cooled to After drying at 25 C, filtration and 50 C, 6.12 g of compound I was obtained. The purity of the solution was 98.66% by HPLC, the impurity was 0.60%, and the impurities V and VI were not detected. The yield was 85.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.6% | With propionic acid; In isopropyl alcohol; for 7.5h;Reflux; | 10.0 g of the compound, 8.16 g of 4-(2-aminoethyl)benzenesulfonamide, 3.02 g of propionic acid and 50 g of isopropanol were heated under reflux for 7.5 h, cooled at 25 C, filtered and dried at 50 C to give the compound 113.52 g. , the yield was 94.4%, the purity of the HPLC method was 99.63%, the impurity was 0.06%, and the impurities V and VI were not detected. |
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