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CAS No. : | 174227-14-6 | MDL No. : | MFCD25977341 |
Formula : | C25H25N5O5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 507.56 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P501-P202-P201-P280-P308+P313-P405 | UN#: | |
Hazard Statements: | H361 | Packing Group: | |
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 |
---|---|---|
Example 1 : Preparation of 4-tert-butyl-N-(6-(2-hydroxyethoxy)-5-(2- methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide, Bosentan by coupling with <strong>[3741-38-6]ethylene sulphite</strong>.; To a mixture of 0.98 g (1.93 mmol) of 4-tert-butyl-N-(6-hydroxy-5-(2- methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide (lib), 0.30 g (2.15 mmol) of K2CO3 and 30 mg (0.09 mmol) of tetrabutylammonium bromide in 5 ml. of methylethylketone was added 0.18 ml. (2.33 mmol, 1.2 equiv) of <strong>[3741-38-6]ethylene sulphite</strong>. The suspension was heated to reflux and stirred until no starting material was observed by TLC. The solvent was eliminated at reduced pressure and the residue dissolved in ethyl acetate. The product was extracted with a solution of NaOH 1 M and the aqueous phase neutralized with acetic acid, extracted to ethyl acetate and washed with NaHCO3 and diluted acetic acid. The organic extracts were dried with anhydrous Na2SO4, filtered and the solvent evaporated under reduced pressure. The product was recrystallised from ethanol/water. |
Yield | Reaction Conditions | Operation in experiment |
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With sodium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide With sodium carbonate In N,N-dimethyl-formamide at 115℃; for 4h; Stage #2: 2-chloro-ethanol In N,N-dimethyl-formamide for 16h; | A mixture of 5 (38.5 g, 0.075 mol) in dimethylformamide (450 ml), sodium carbonate(32.15 g, 0.303 mol) was heated to (∼115C) for 4 h. 2-Chloroethanol (30.53 g, 0.379 mol)was then added and the mixture was stirred for 16 h. Water (∼400 ml) was added and thereaction mixture was then acidified with 6N HCl to a pH ∼ 2.0. The reaction mixture wasstirred for 10 min and extracted with methylene chloride (700 ml). The organic layer wasseparated, and the aqueous layer was extracted with toluene (∼200 ml). The organic layerswere combined, dried over sodium sulfate and evaporated under reduced pressure. The solidresidue was dissolved in methanol (150 ml) and stirred for 30 min. The reaction mixturewas then added to water (200 ml) and stirred for 4 h. The solid which precipitated out wascollected and dried to afford bosentan 4. (36.0 g, 86% yield) as a solid, mp. 138-140C.HPLC Purity: 99.70%. Water content: 3.2% (w/w). MS: m/z: 552 (M-OH). 1H-NMR: δ1.29 (s, 9H), 3.86 (s, 2H), 3.94 (s, 3H), 4.57 (m, 2H), 4.88 (s,1H), 6.85 (m, 1H), 7.10 (m,2H), 7.15 (m, 1H), 7.41(m, 3H), 8.42 (d, 2H, J = 4.9 Hz), 9.0 (d, 2H, J = 4.9Hz). IR:3437.4, (NH), 1342 cm-1 (SO2).Anal. Calcd for C27H31N5O7S: C, 56.93; H, 5.49; N, 12.29. Found: C, 56.68; H, 5.25;N, 12.48. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; 2-chloro-ethanol In N,N-dimethyl-formamide |