Structure of 63134-33-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 63134-33-8 |
Formula : | C19H16O4S |
M.W : | 340.39 |
SMILES Code : | OC1=CC=C(S(=O)(C2=CC=C(OCC3=CC=CC=C3)C=C2)=O)C=C1 |
MDL No. : | MFCD00185925 |
InChI Key : | UWPJWCBDMZHMTN-UHFFFAOYSA-N |
Pubchem ID : | 113063 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 |
* 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 |
---|---|---|
16% | With sodium hydroxide; In water; at 80.0℃; for 24.0h;Inert atmosphere; | General procedure: Bisphenol A (20mmol, 4.566g) was added to a 250mL round bottom flask containing NaOH aqueous solution (40mmol, 150mL, 1.599g). The reactor was then equipped with a reflux condenser and brought to 80C in a nitrogen environment with vigorous stirring via a Teflon-coated magnetic stir bar. Once completely dissolved, benzyl bromide (20mmol, 0.342g) was added via syringe. The mixture was allowed to stir for 2h at 80C in a nitrogen environment. After stirring was ceased, a beige precipitate settled out in a clear solution. While still hot, the supernatant was decanted and the crude product washed with water (ca. 80C). The crude product was then dissolved in chloroform, transferred to a separatory funnel, washed w/10% HCl (v/v), and then washed twice with DI H2O. The organic layer was then dried over magnesium sulfate, filtered into a tared receiver flask, and isolated under vacuum as an off-white solid. The compound was then recrystallized twice from hexanes/ethyl acetate to afford a white, crystalline solid (3.80g, 59.7% yield, mp (DSC)=109C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In sodium hydroxide; toluene; | EXAMPLE 2 Synthesis of 4-benzyloxy-4'-(2-methylglycidyloxy)diphenylsulfone [compound (1)] (another process) An amount of 66 g of 2-methylepichlorohydrin, 1 g of tetrabutytammonium bromide as a catalyst and 34. 0 of <strong>[63134-33-8]4-benzyloxy-4'-hydroxydiphenylsulfone</strong> were added and reacted at 85-90 C. for 6 hours. After evaporating 2-methylepichlorohydrin, residual matter was dissolved in 300 ml of toluene, in which 20% sodium hydroxide aqueous solution was added, and the mixture was reacted at 80 C. for 30 minutes. After the aqueous layer was separated and discarded, the organic layer was heated at 105 C. to complete the reaction. After cooling, 4-benzyloxy-4'-(2-methylglycidyloxy) diphenylsulfone was separated by filtration and obtained as 36 g of the crystal. The melting point of the crystal was 164-167 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Specific examples of such electron accepting compounds are as follows: ... 1,1,3-tris(2-methyl-4-hydroxy-5-cyclohexylphenyl)butane, 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-diphenolsulfone, 4-isopropoxy-4'-hydroxydiphenylsulfone, 4-benzyloxy-4'-hydroxydiphenylsulfone, 4,4'-diphenolsulfoxide, isopropyl p-hydroxybenzoate, benzyl p-hydroxybenzoate, ... | ||
Specific examples of the color developer for use in the present invention are as follows: ... 3,4'-dihydroxy-4'-methyldiphenylsulfone, 4-isopropoxy-4'-hydroxydiphenylsulfone, 4-benzyloxy-4'-hydroxydiphenylsulfone, 4,4'-diphenolsulfoxide, ... | ||
Preferably exemplified are 4,4'-isopropylidenediphenol, ... bis(3-allyl-4-hydroxyphenyl)sulfone, 4-hydroxy-4'-isopropoxydiphenylsulfone, 4-hydroxy-4'-n-propoxydiphenylsulfone, 4-hydroxy-4'-allyloxydiphenylsulfone, 4-hydroxy-4'-benzyloxydiphenylsulfone, 3,4-dihydroxyphenyl-4'-methylphenylsulfone, N-(2-hydroxyphenyl)-2-[(4-hydroxyphenyl)thio]acetamide, |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In sodium hydroxide; | Example 3. (Synthesis of compound I- 56 in Table 1) According to similar synthetic method as phenyl glycidyl ether in example 1, 4-benzyloxy-4'-(2-methylglycidyloxy) diphenylsulfone was obtained by reacting with <strong>[63134-33-8]4-benzyloxy-4'-hydroxydiphenylsulfone</strong> and 2-methylepichlorohydrin in sodium hydroxide aqueous solution. Five grams of the compound and 2.3 g of p-phenylphenol were similarly reacted as example 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N-methyl-acetamide; sodium hydroxide; | Example 2. (Synthesis of compound I- 10 in Table 1) According to similar synthetic method as phenyl glycidyl ether in example 1, 4-benzyloxy-4'-glycidyloxydiphenyl-sulfone was obtained by reacting <strong>[63134-33-8]4-benzyloxy-4'-hydroxydiphenylsulfone</strong> and epichlorohydrin in sodium hydroxide aqueous solution. In 10ml of dimethylformamide, 5 g of the obtained compound was dissolved. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate; In ethyl acetate; N,N-dimethyl-formamide; | Example 9 (Synthesis of (IV)-93 by Using (I)-19) 3.0 g (0.022 mol) of α-chloropinacolone and 6.8 g (0.02 mol) of 4-(4-benzyloxyphenylsulfonyl)phenol were dispersed in 50 ml of N,N-dimethylformamide, and then 3.1 g (0.022 mol) of potassium carbonate was added to the dispersion, followed by heating on a steam bath for 2 hours with stirring. The temperature was brought to room temperature; 200 ml of ethyl acetate was added thereto; the organic layer was washed with water; then the solvent was removed by distillation, and the residue was crystallized from acetonitrile, to obtain 8.7 g of colorless crystals of 4-(4-benzyloxyphenylsulfonyl)phenoxypinacolone. Melting point: 195-197C. Yield: 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | With sodium hydroxide; In water; at 80.0℃; for 24.0h;Inert atmosphere; | Synthesis was analogous to compound 1 with an extended reaction time of 24 h. Significant amounts of di-benzyl protected side product was produced, requiring purification by column chromatography (silica/90:10 DCM:MeOH, Rf = 0.67) to afford awhite, crystalline solid (215 mg, 16% yield, mp (DSC) = 92.3 8C).ATR-FTIR (neat, cm1): 3570, 3380, 3100, 3070, 3040, 2950, 2900,2860, 2830, 1590, 1500, 1460, 1420, 1380, 1290, 1250, 1150, 1110,1080, 1030, 1010, 845, 829, 744, 727, 702, 665, 600, 553. 1H NMR(d, ppm, 500 MHz, acetone-d6): 5.27 (s, -CH2Ph, 2H), 7.09 (d, 2H,3JHH = 8.7 Hz), 7.25 (d, 2H, 3JHH = 8.9 Hz), 7.40-7.55 (m, 5H), 7.91(d, 2H, 3JHH = 8.7 Hz), 7.97 (d, 2H, 3JHH = 8.9 Hz), 9.45 (s, OH, 1H).13C (d, ppm, 125 MHz, acetone-d6): 70.9, 116.2, 116.7, 128.5, 128.9,129.3, 130.2, 130.6, 134.2, 135.8, 137.4, 162.3, 163.1. |
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