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CAS No. : | 582-25-2 | MDL No. : | MFCD00013061 |
Formula : | C7H5KO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XAEFZNCEHLXOMS-UHFFFAOYSA-M |
M.W : | 160.21 | Pubchem ID : | 23661960 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 31.46 |
TPSA : | 40.13 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.95 cm/s |
Log Po/w (iLOGP) : | -3.89 |
Log Po/w (XLOGP3) : | 1.87 |
Log Po/w (WLOGP) : | 0.05 |
Log Po/w (MLOGP) : | 1.6 |
Log Po/w (SILICOS-IT) : | 1.24 |
Consensus Log Po/w : | 0.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.39 |
Solubility : | 0.654 mg/ml ; 0.00408 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.33 |
Solubility : | 0.742 mg/ml ; 0.00463 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.72 |
Solubility : | 3.02 mg/ml ; 0.0189 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Danger | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338+P310-P332+P313-P362+P364 | UN#: | N/A |
Hazard Statements: | H315-H318 | Packing Group: | N/A |
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 |
---|---|---|
395 g | at 90 - 135℃; | To the solution of 210g of potassium benzoate in 1700ml of N-methyl pyrrolidine was added 3.36g of l -(3-chloropropyl)-5-(2-nitropropyl)indoline-7-carbonitrile at 90-135°C. Stirred the reaction mass under heating, cooled to room temperature and added D.M water followed by extraction of compound in toluene. Combined the organic layer and concentrated under reduced pressure to get 395g of desired indoline compound. 1HNMR (CDC1.3): δ 8.04 (2H, dd), 7.55(1H, t), 7.45(211. t), 6.93(1H, s), 6.88(1H, s), 4.64- 4.69(1H, m), 4.47(2H, t), 3.76(2H, t), 3.61(2H, t), 3.08-3.14(1H, m), 2.96(2H, t), 2.82- 2.87(1H, m), 2.12-2.19(2H, m), 1 .54(311. d). m z(M+l): 394.55 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium iodide; In DMF (N,N-dimethyl-formamide); for 20h;Heating / reflux; | EXAMPLE 1 Preparation of 2-benzoyloxyacetaldehyde dimethyl acetal Chloroacetaldehyde dimethyl acetal (50.0 g), <strong>[582-25-2]potassium benzoate</strong> (70.7 g), potassium iodide (6.66 g) and DMF (N,N-dimethylformamide) (250 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (250 mL) and ethyl acetate (250 mL) were added thereto, followed by stirring. After filtration, the filtrate was extracted with ethyl acetate (500 mL). The organic layer was subjected to vacuum concentration and then to vacuum distillation at 132-135 C. and at 5 mmHg and thereby yielded the target compound (61.0 g) in a yield of 72%. 1H-NMR (CDCl3) delta: 8.06 (m, 2H), 7.56 (m, 1H), 7.44 (m, 2H), 4.72 (t, 1H), 4.36 (d, 2H), 3.44 (s, 6H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium acetate; potassium phthalate;zinc(II) oxide; at 450℃; under 25858.1 Torr; | Potassium acetate, which melts (Condensed Chemical Dictionary, 6th edition) at 292C, was used as a molten reaction medium for the Henkel reaction of <strong>[582-25-2]potassium benzoate</strong> with and without ZnO as catalyst. It was thought that since the salt melts at a lower temperature than the carbonate eutectics, it might be possible to perform the reaction at a lower temperature. However, little Henkel reaction was observed at temperatures significantly below 400C. Unexpectedly, however, on examining the reaction products of the black fused mass formed from the potassium acetate salt and the naphthoic or benzoate potassium salts at ca. 400C and above, a significant portion of methylated diacids was observed. Thus, from a reaction conducted at 450C and 500 psi of CO2 containing the following ingredients, 50g of potassium acetate, 5g of potassium phthalate, 1g of ZnO, a yield of about 50% of TPA and 20% of methylated TPA was unexpectedly observed. The methylated TPA was a mixture of 2-methyl 1,4 dicarboxy benzene, 2,5 dimethyl 1,4 dicarboxybenzene, 2,3,5 trimethyl 1,4 dicarboxy benzene, and 2,3,5,6 tetramethyl 1,4 dicarboxy benzene. The initial product appeared to be the 2-methyl species, however again surprisingly, the major components were the 2,5 dimethyl and the tetramethyl TPA (permethyl TPA). A possible explanation of this result is that the symmetrically di- or tetra- substituted salts are more stable or form particles which are more isolated from the reaction medium. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: To a solution of disulfonate 4 (1 equiv) in DMF (0.1-0.15 M) was added <strong>[582-25-2]KOBz</strong> (1.2-4.2 equiv), and the reaction mixture was heated at 100 C until no further reaction was evident by TLC (12 h for 4a-c, 8 h for 4d). The mixture was allowed to cool down to room temperature, poured into cold water and extracted with a 1:1 mixture of benzene/light petroleum. The combined extracts were washed with water, dried and evaporated. The residue was then purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In N,N-dimethyl-formamide; at 100℃; for 8h; | General procedure: To a solution of disulfonate 4 (1 equiv) in DMF (0.1-0.15 M) was added <strong>[582-25-2]KOBz</strong> (1.2-4.2 equiv), and the reaction mixture was heated at 100 C until no further reaction was evident by TLC (12 h for 4a-c, 8 h for 4d). The mixture was allowed to cool down to room temperature, poured into cold water and extracted with a 1:1 mixture of benzene/light petroleum. The combined extracts were washed with water, dried and evaporated. The residue was then purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium iodide; In N,N-dimethyl-formamide; for 20h;Heating / reflux;Product distribution / selectivity; | EXAMPLE 2 Preparation of 2-benzoyloxyacetaldehyde diethyl acetal Chloroacetaldehyde diethyl acetal (2.00 g), <strong>[582-25-2]potassium benzoate</strong> (1.91 g), potassium iodide (0.41 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was separated, was subjected to vacuum concentration and then to Kugelrohr distillation at 110-120 C. and at 1 mmHg and thereby yielded the target compound (2.41 g) in a yield of 77%. |
31% | With potassium bromide; In N,N-dimethyl-formamide; for 20h;Heating / reflux;Product distribution / selectivity; | EXAMPLE 3 Preparation of 2-benzoyloxyacetaldehyde diethyl acetal Chloroacetaldehyde diethyl acetal (2.00 g), <strong>[582-25-2]potassium benzoate</strong> (1.91 g), potassium bromide (0.30 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was washed with water (30 mL) and was dried over anhydrous sodium sulfate. Subsequent filtration and vacuum concentration yielded the target compound (0.97 g) in a yield of 31%. |
30% | In N,N-dimethyl-formamide; for 20h;Heating / reflux;Product distribution / selectivity; | COMPARATIVE EXAMPLE 1 Preparation of 2-benzoyloxyacetaldehyde diethyl acetal Chloroacetaldehyde diethyl acetal (1.9 g), <strong>[582-25-2]potassium benzoate</strong> (2.0 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (60 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration and separation, the organic layer was concentrated and thereby yielded the target compound (0.69 g) in a yield of 30%. While the present invention has been described with reference to what are presently considered to be the preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. On the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The scope of the following claims is to be accorded the broadest interpretation so as to encompass all such modifications and equivalent structures and functions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphoric acid; In hexane; water; dimethyl sulfoxide; mineral oil; | EXAMPLE 1 (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine, phosphoric acid salt A 13.5 g portion of (S)-(-)-N,N-dimethyl-3-hydroxy-3-(2-thienyl)propanamine was dissolved in 80 ml of dimethylsulfoxide at 25° C. To the solution was slowly added 3 g of sodium hydride as a 60percent dispersion in mineral oil, with vigorous stirring. After 15 minutes of stirring, 1.17 g of potassium benzoate was added and stirring was continued at approximately constant temperature for another 15 minutes. Then, 12.8 g of 1-fluoronaphthalene was slowly added to the reaction mixture, and after the addition was complete, the mixture was heated and was stirred for 2.5 hours at 60°-65° C. The mixture was then poured slowly into 190 ml of cold water and the DH was adjusted to 4.8 by addition of acetic acid. The temperature of the mixture was brought to 25° C., and 75 ml of hexane was added and stirring was continued for 10 minutes. The layers were then separated and the aqueous phase was stirred again with 75 ml of hexane and the phases separated. The pH of the aqueous phase was adjusted to 10.2 by addition of aqueous sodium hydroxide, and 75 ml of ethyl acetate was added. That mixture was stirred for 15 minutes at 25° C., and the 2-phase mixture was vacuum filtered through a pad of filter aid. The phases of the filtrate were allowed to separate, and the aqueous phase was extracted with 75 ml of ethyl acetate. The extract was combined with the previous ethyl acetate layer, and that mixture was washed with 100 ml of water. The organic layer was stirred at 25° C., and to it was added, dropwise, 7 g of 85percent phosphoric acid. After the addition was complete, the mixture was stirred for 20 minutes more and was then cooled to 0° C. and stirred for 1 hour at that temperature. The slurry was then filtered and the solids washed three times with 20 ml portions of cold ethyl acetate. The solid was dried at 60° C. to afford 24.19 g of the title compound as a white solid, 98.1percent potency, adjusted yield 79.6percent, 91percent EE. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate; | EXAMPLE 10 4-Chlorophthalic anhydride (10 g, 55 mmol), potassium benzoate (1.0 g, 6.2 mmol), and N-methylpyrrolidinone (25 g) were heated to about 175.C. Potassium carbonate (3.87 g, 28 mmol) was added and the suspension was heated to about 175.C. After 2 hours, GC analysis indicated a greater than 97% conversion to 4,4'-oxydiphthalic anhydride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(I) iodide; In 1-methyl-pyrrolidin-2-one; | EXAMPLE 66 420 mg of 5-chloro-6-nitro-beta-carboline-3-carboxylic-acid-ethylester, 40 mg of cuprous iodide and 130 mg of potassium benzylate in 8 ml of N-methylpyrrolidone are heated for 7 h at 70 C. After the solvent is distilled off, the residue is chromatographed on silica gel with toluene/glacial-acetic-acid/water (10/10/1). 280 mg of 5-benzyloxy-6-nitro-beta-carboline-3-carboxylic-acid-ethylester with a m.p. of 254 C. (dissociation) is obtained. | |
With copper(I) iodide; In 1-methyl-pyrrolidin-2-one; | EXAMPLE 66 420 mg of 5-chloro-6-nitro-beta-carboline-3-carboxylic-acid-ethylester, 40 mg of cuprous iodide and 130 mg of potassium benzylate in 8 ml of N-methylpyrrolidone are heated for 7 h at 70 C. After the solvent is distilled off, the residue is chromatographed on silica gel with toluene/glacial-acetic-acid/water (10/10/1). 280 mg of 5-benzyloxy-6-nitro-beta-carboline-3-carboxylic-acid-ethylester with a m.p. of 254 C. (dissociation) is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In tetrahydrofuran; | EXAMPLE 10 Potassium benzoate The procedure of Example 1 was followed using phenyl benzoate (3.96 g, 20 mmol), <strong>[10519-96-7]potassium trimethylsilanolate</strong> (2.56 g, 20 mmol), dry tetrahydrofuran (50 mL), and a 5 h reaction time. Potassium benzoate (2.37 g, 74% yield) was isolated as a white solid: 1 H NMR (D2 O, DSS, 80 MHz) delta 7.4-8.0 (m, Ar--H's, 5H). Anal. Calcd. for C7 H5 KO2: C, 52.48; H, 3.15; K, 24.41, Found: C, 50.28, 50.15, 52.45; H, 3.28, 3.36, 3.24; K, 24.80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In ice-water; dichloromethane; | (b) Isosorbide-2-benzoate 1073.0 g of isomannide-2-p-toluenesulfonic acid ester and 574.7 g of <strong>[582-25-2]potassium benzoate</strong> in 2.8 l of dimethylformaide are refluxed with stirring for 2 to 4 hours. The resulting reaction mixture is cooled to 100 to 110 C. and poured upon 10 l of ice-water. The mixture is extracted three times with each 2 l methylene dichloride. The combined extracts are washed twice with each 1.5 l of a saturated aqueous solution of sodium hydrogencarbonate NaHCO3 and once with 1.5 l of 1 N hydrochloric acid. The resulting methylene dichloride solution is heated to boiling with 88 g of activated charcoal, filtered and evaporated. There are obtained about 850 g of oily yellow-brownish isosorbide-2-benzoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98.5% | With sodium carbonate; In ISOPROPYLAMIDE; | EXAMPLE 7 A 250 ml flask equipped with an agitator, thermometer, and nitrogen bleed is charged with 66.5 (0.47 mole) p-fluoronitrobenzene, 77 g dimethylacetamide, 0.57 g (0.004 mole) <strong>[582-25-2]potassium benzoate</strong> and 25 g (0.24 mole) sodium carbonate. The reaction mixture is heated to and maintained at 170 C. while it is agitated and kept under a nitrogen blanket. After 12 hours 4,4'-dinitrodiphenyl ether is obtained in 98.5% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With HCl (g); NaH; In water; dimethyl sulfoxide; ethyl acetate; | Step B A 1 L jacketed flask was charged with NaH (60 % oil dispersion, 31.7 g, 0.792 mol), potassium benzoate (13.0 g, 0.0809 mol), and DMSO (133.6 mL). To this vessel was added a solution N-methyl-3R-hydroxy-3-phenylpropylamine (133.6 g, 0.809 mol) in 133.6 mL DMSO over 45 minutes followed by a 66.8 mL DMSO rinse. The resulting mixture stirred for 10 minutes. To this vessel was added 2-fluorothioanisole (126.5 g, 0.890 mol) followed by an additional rinse with 66.8 mL of DMSO. The reaction mixture was heated to 65C and stirred for 18.8 hours. The reaction was then cooled to room temperature and added to a quench solution consisting of 0.9 L of H2O and 0.7 L EtOAc followed by an additional rinse with 0.23 L H2O and 0.18 L EtOAc. The layers were separated and the aqueous layer was extracted with 0.38 L EtOAc. The combined EtOAc layers were washed with 0.67 L each of H2O and saturated aqueous NaCl. The EtOAc layer was dried over Na2SO4and filtered. The Na2SO4was washed with 0.13 L EtOAc. The filtrate was cooled to approximately 0C and HCl (g) (29.52 g) was added. The thick slurry thus formed was stirred an additional 30 minutes and the crystals were collected by filtration, washed with 0.27 L of cold EtOAc, and placed in a vacuum oven at 35-40C. G (233.1 g) was recrystallized from EtOH (0.700 L) which provided 188.3 g of N-methyl3R-(2-methylthiophenoxy)-3-phenylpropylamine hydrochloride in 99.6 % ee. 1H NMR (CDCl3): delta 9.64 (br s, 2 H), 7.40-7.20 (m, 5H), 7.15-7.05 (m, 1H), 6.95-6.82 (m, 2H), 6.65-6.55 (m, 1H), 5.45 (dd, 1H), 3.32-3.18 (m, 2H), 2.66 (t, 3H), 2.56-2.42 (m, 5H). Calcd. for C17H22ClNOS: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium hydroxide; In ethanol; at 20℃; for 72h; | A mixture of enc/o-3-benzoyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid te/f-butyl ester (55.0 g, 166 mmol), potassium hydroxide (11.2 g 199 mmol) and ethanol (99%, 30 400 ml) was stirred for 3 days at room temperature. Potassium benzoate was separated by filtration and the filtrate was evaporated. Diethylether (200 ml) was added and remaining potassium benzoate was separated by filtration and the filtrate was evaporated. The product was triturated with petroleum. Yield 30.0 g (80%). Mp 139.5- 140.80C |
80% | With potassium hydroxide; In ethanol; at 20℃; for 72h; | A mixture of enc/o-3-benzoyloxy-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid te/f-butyl ester (55.0 g, 166 mmol), potassium hydroxide (11.2 g 199 mmol) and ethanol (99%, 400 ml) was stirred for 3 days at room temperature. Potassium benzoate was separated by filtration and the filtrate was evaporated. Diethylether (200 ml) was added and remaining potassium benzoate was separated by filtration and the filtrate was evapo- rated. The product was triturated with petroleum. Yield 30.0 g (80%). Mp 139.5- 140.80C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.1% | In N,N-dimethyl-formamide; at 20 - 80℃; for 16.5h;Inert atmosphere; | The bromo compound 6 (1 g, 2.32 mmol) was dissolved in DMF (20 mL) and anhydrous <strong>[582-25-2]potassium benzoate</strong> (1.115 g, 6.96 mmol) was added while stirring. The suspension was gradually heated under argon in an oil bath to 80 C (30 min), and maintained at that temperature for 16 h. It was cooled to room temperature and diluted with H2O. The aqueous phase was extracted with Et2O. The combined organic extracts were washed with H2O dried over Na2SO4, and the solvent removed in vacuo. Column chromatography of the crude material with hexane and EtOAc (5:1) gave the ester 7 (1.58 g, 68.1%). The HCl salt was prepared and recrystallized from MeOH. Mp (HCl salt) 98.1-99.2 C; 1H NMR (CDCl3, 300 MHz): delta 7.64 (d, J = 7.5 Hz, 2H), 7.43(d, J = 7.5 Hz, 2H), 7.20-7.31 (m, 6H), 6.96 (m, 2H), 6.83 (dd, J = 6.9, 2.7 Hz, 1H), 4.64 (m, 2H), 4.15 (d, J = 13.8 Hz, 1H), 3.98 (t, J = 6.3 Hz, 1H), 3.89 (s, 3H), 3.88 (m, 1H), 3.84 (s, 3H), 3.11 (t, J = 5.1 Hz, 1H), 2.69 (m, 1H), 1.94-2.22 (m, 3H), 1.45-1.79 (m, 3H), 1.25 (m, 1H); 13C NMR (CDCl3, 75 MHz): delta 166.61, 153.33, 148.43, 141.40, 138.14, 132.53, 130.21, 129.48, 128.37, 128.04, 126.59, 123.20, 119.94, 111.13, 69.98, 65.88, 62.21, 60.63, 60.10, 55.79, 49.33, 41.46, 31.91, 31.34, 20.41; HRMS calcd for C30H34NO4 [M+H]+: 472.2488; found: 472.2493. Anal. Calcd for C30H33NO4·HCl·1.1H2O: C, 68.26; H, 6.91; N, 2.65. Found: C, 68.06; H, 6.82; N, 2.65. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: To a solution of disulfonate 4 (1 equiv) in DMF (0.1-0.15 M) was added <strong>[582-25-2]KOBz</strong> (1.2-4.2 equiv), and the reaction mixture was heated at 100 C until no further reaction was evident by TLC (12 h for 4a-c, 8 h for 4d). The mixture was allowed to cool down to room temperature, poured into cold water and extracted with a 1:1 mixture of benzene/light petroleum. The combined extracts were washed with water, dried and evaporated. The residue was then purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In N,N-dimethyl-formamide; at 100℃; for 12h; | General procedure: To a solution of disulfonate 4 (1 equiv) in DMF (0.1-0.15 M) was added <strong>[582-25-2]KOBz</strong> (1.2-4.2 equiv), and the reaction mixture was heated at 100 C until no further reaction was evident by TLC (12 h for 4a-c, 8 h for 4d). The mixture was allowed to cool down to room temperature, poured into cold water and extracted with a 1:1 mixture of benzene/light petroleum. The combined extracts were washed with water, dried and evaporated. The residue was then purified by silica gel column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With benzoic acid; In N,N-dimethyl-formamide; at 110 - 120℃; for 2h;Inert atmosphere; | To a stirred solution of kojyl chloride9 (4.80 g, 30.0 mmol) in DMF (100 mL) under N2 potassiumsalt of benzoic acid (4.79 g, 30.0 mmol) with benzoicacid (2.73 g, 2.25 mmol) was added. The reaction mixturewas stirred for 2 h at 110-120C, after which DMF wasevaporated in vacuo. The residue was extracted with ethylacetate (500 mL), and then was washed with water. Theorganic layer was dried with anhydrous MgSO4 and concentratedto give a crude product. The resultant was purifiedby crystallization from ethyl acetate-hexane to give10a (5.37 g) in 73% yields. 1H NMR (300 MHz, DMSOd6):delta 9.29 (s, 1H), 8.11 (s, 1H), 8.02 (m, 2H), 7.71 (m,1H), 7.58 (m, 2H), 6.55 (s, 1H), 5.22 (s, 2H). 13C-NMR(125 MHz, DMSO-d6): 173.5, 164.9, 161.4, 146.0, 139.9,133.7, 129.3, 128.8, 128.7, 112.6, 61.9. FABMS, m/e245.1 [M-H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In N,N-dimethyl-formamide; at 130℃; for 5h; | A mixture of bromo compound 7[6] (4.1 g, 12.64 mmol) and <strong>[582-25-2]potassium benzoate</strong> (10.1 g, 63.22 mmol) was heated in DMF at 130 C for 5 h. After cooling to room temperature, the reaction mixture was diluted with water and the organic layer was extracted into ether dried over Na2SO4 and solvent was evaporated. The crude material was purified by flash chromatography using 30% ether in hexanes as an eluent. Compound 10 was obtained as an orange solid (3.0 g, 67%). A small batch was treated with HBr in methanol to give a white crystalline 10.HBr. Mp 251-253 C; 1H NMR (CDCl3, 500 MHz) delta 7.76 (d, 2H, J = 8.0 Hz), 7.49 (t, 1H, J = 7.0 Hz), 7.33 (t, 2H, J = 7.5 Hz), 7.22 (t, 1H, J = 8.0 Hz), 7.03 (d, 1H, J = 8.0 Hz), 6.98 (s, 1H), 6.72 (d, 1H, J = 8.0 Hz), 4.54 (m, 2H), 3.17 (t, 1H, J = 6.0 Hz), 3.13 (t, 1H, J = 5.0 Hz), 2.69 (s, 3H), 2.45 (t, 1H, J = 7.0 Hz), 2.17 (m, 1H), 2.04 (m, 1H), 1.79 (m, 3H), 1.56 (d, 1H, J = 11.5 Hz), 1.36 (dt, 1H, J = 5.5 and 12.5 Hz); 13C NMR (CDCl3, 126 MHz) delta 166.69, 159.70, 147.07, 132.82, 130.19, 129.66 (2C), 129.33, 128.23 (2C), 118.40, 112.84, 110.59, 75.32, 65.12, 63.78, 55.31, 49.93, 46.34, 43.37, 31.29, 30.25, 19.97; HRMS (TOF MS ES+) calcd for C23H28NO3 (M + H)+: 366.2069; found: 366.2071. Anal. C23H27NO3·HBr·0.5H2O (C, H, N). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With oxygen; copper diacetate; silver carbonate; In N,N-dimethyl-formamide; at 140℃; under 750.075 Torr; for 36h; | General procedure: A 70 mL teflon-screw capped schlenk tube was charged with potassium carboxylate (1l-z) (1.00 mmol), copper(II) acetate (46 mg, 0.25 mmol), silver carbonate (276 mg, 1 mmol), and alkoxy borane (4a-h) (1.2 mmol). Anhydrous DMF (5 mL) was added, the reaction vessel was briefly purged with oxygen, and the resulting mixture was stirred at 140 C for 36 h. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (20 mL) and washed with saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was extracted with diethyl ether (3 x 20 mL), and the combined organic layers were washed with water, 5 N HCl and brine, dried over MgSO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography on silica gel to yield the corresponding aryl ether (3la...3xh). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With tetrabutylammomium bromide; In toluene; for 5h;Reflux; | General procedure: In a 100 mL round-bottomed flask, epichlorohydrin (4) (38 mmol), sodium or potassium salt of the corresponding carboxylic acid (25 mmol), and TBAB (0.84 mmol) were dissolved in an appropriate solvent (20 mL). The mixture was remained under reflux for 5 hours. Reaction in toluene: the reaction mixture was placed in a separatory funnel, washed with water (50 mL), saturated sodium bicarbonate solution (50 mL) and, washed with water (50 mL) again. The organic layer was dried over anhydrous magnesium sulfate, filtered and subjected to distillation under reduced pressure. Reaction in acetonitrile: the mixture was concentrated in a rotary evaporator under reduced pressure, ethyl acetate (50 mL) was added to the residue and, washed with water (100 mL), saturated sodium bicarbonate solution (50 mL) and, washed with water (100 mL) again. The organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was removed on a rotary evaporator |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In dimethyl sulfoxide; at 70℃; for 0.833333h; | (4) (1.42 g, 3.5 mmol) of (R, Z) -1-(tert-butoxydiphenylsilyloxy) -6-chloro-4- fluoro-4-hexen-Of dimethylsulfoxide (14 ml)To the solution was added <strong>[582-25-2]potassium benzoate</strong> (1.13 g, 7.0mmol)Was added.Next, the reaction was carried out at 70 C. for 50 minutes,The reaction solution was added to water (20 ml), extractedwith diethyl ether (30 ml × 3 times), combined with the organic layer, washedwith saturated brine (20 ml), dried over magnesium sulfate, filtered andconcentrated under reduced pressure to obtain a crude product .The obtained crude product was purified by silica gel columnchromatography (hexane / ethyl acetate = 20/1 vol / vol) to obtain theobjective product (R, Z) -6- (tert- butyldiphenylsilyloxy) -3-Hydroxo-4-hydroxy-2-hexen-1-yl benzoate was obtained as a colorless transparentliquid (1.23 g, 2.50 mmol, yield 98% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.1% | In acetonitrile; for 10h;Reflux; | To a suspension of <strong>[582-25-2]potassium benzoate</strong> (1.60 g, 10 mmol) in acetonitrile (60 mL), was added 1,3-dibromopropane (2.04 mL, 20 mmol). Then refluxing for 10h. After cooling to room temperature, the solution was concentrated, and the resultant residue was purified by column chromatography (10% ethyl acetate/ petroleum ether) to yield colorless oil. 75.1%.1H-NMR (400 MHz, CDCl3) delta 8.03-8.05 (d,J= 7.1 Hz, 2H), 7.55-7.59 (t,J= 7.4 Hz, 1H), 7.43-7.47 (t,J= 7.6 Hz, 2H), 4.46-4.49 (t,J= 6.0 Hz, 2H), 3.54-3.57 (t,J= 6.6 Hz, 2H), 2.30-2.36 (p,J= 6.4 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In acetonitrile; at 48℃;Reflux; | A mixture of 8 (2.03 g, 4.63 mmol) and <strong>[582-25-2]BzOK</strong> (1.5 g, 9.26 mmol) was stirred in CH3CN (20 mL) at refluxing temperature for 48 h. The mixture was diluted with H2O (50 mL), followed by extraction with EtOAc (3 * 30 mL). The combined organic phase was then washed with water (3 * 10 mL) and brine (10 mL). After concentration in vacuo, the residue was purified by silica gel column chromatography (25% EtOAc/PE) to afford 9 (1.53 g, 69%) as a white solid. mp 42-43 C. 1H NMR (400 MHz, CDCl3) delta 8.04 (m, 3H, Ar-H), 7.54 (br t, J = 7.5 Hz, 1H, Ar-H), 7.41 (br t, J = 7.5 Hz, 2H, Ar-H), 6.51 (dd, J = 8.7, 2.2 Hz, 1H, Ar-H), 6.49 (d, J = 2.2 Hz, 1H, Ar-H), 6.46 (d, J = 2.0 Hz, 1H, Ar-H), 6.37 (d, J = 2.0 Hz, 1H, Ar-H), 5.28 (s, 2H, CH2), 3.89 (s, 3H, OCH3), 3.86 (s, 3H, OCH3), 3.85 (s, 3H, OCH3), 3.83 (s, 3H, OCH3). 13C NMR (150 MHz, CDCl3) delta 194.0, 165.8, 165.0, 163.1, 162.9, 162.3, 159.6, 151.3, 135.1, 133.0, 129.9, 129.9, 128.3, 128.3, 113.7, 111.0, 104.9, 101.0, 99.0, 96.3, 69.6, 56.0, 56.0, 55.7, 55.5. IR (neat): nu 2923, 1727, 1609, 1419, 1213, 830, 712 cm-1. HRMS (ESI) calcd mass for C26NH28O9 [M+NH4]+ 498.1759, found 498.1757. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In the 500 mi [...] adding intermediate VIII (5 g, 0.017 muM), adding water 16.5 ml and 40% sodium hydroxide solution of 11 ml, the mixture stirred at room temperature 35.5 h. Is added to the mixture 6 N hydrochloric acid 55 ml, and in the 25 C to 30 C is obtained by stirring a mixture of 48 h, by 2 - deoxy-ribose - L -. The reaction solution in saturated sodium bicarbonate to weakly alkaline pH and is about 8, concentrated to 110 ml added 3.3 g aniline, stirring 6 h. Standing, filtration, solid de-ionized water and methanol washing, drying to obtain the N - phenyl -2 - deoxy - L - nuclear osamine (intermediate IX) (2.23 g, 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-dimethyl-formamide; In water; butan-1-ol; at 120℃; for 12h; | In the 500 mi [...] adding intermediate VII (10 g, 0.022 muM), adding butanol 3 . 56 m1, deionized water 2 ml, N, N - dimethyl formamide 14 ml and benzoic acid potassium 10.61 g, and the reaction mixture is heated to 120 C (reflux), the reaction 12 h. After concentrating the reaction mixture, adding 80 ml ethyl acetate and 80 ml saturated sodium bicarbonate extraction, organic uses 2 * 40 ml of a saturated sodium bicarbonate washing, the aqueous phase is 40 ml ethyl acetate extraction, the combined organic phase turns on lathe does. To obtain the solid, 2 - deoxy - 1 - O - butyl -3 - benzoyl - D - ribose and 2 - deoxy - 1 - O - butyl -3 - - benzoyl - D - ribose (intermediate VIII) (5.38 g, 83.6%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | General procedure: An oven-dried and nitrogen-flushed Schlenk tube equippedwith a mechanical stirrer was charged with potassiumcarboxylate (1.2 mmol), copper(I) bromide (10 mol%),Phen (5 mol%), and 3.0 cm3 DMA. The resulting mixturewas stirred at 120 C for 2 h. Afterwards, the mixture wascharged with Pd2(dba)3 (3 mol%), dppb (12 mol%), andalkynes (1.0 mmol). The Schlenk tube was sealed and thenevacuated and backfilled with Ar (3 cycles). After stirringthe mixture at room temperature for 15 min, AcOH(4.0 mmol) was injected and the reaction was heated to120 C for 22 h. The mixture was cooled to room temperatureand filtered through Celite. The solid was rinsedwith 50 cm3 ethyl acetate and the resulting filtrate wasconcentrated under vacuum. The residues were purified bycolumn chromatography on silica gel (eluent: petroleumether/ethyl acetate, gradient 20:1 to 5:1) furnishing 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With tetrabutylammomium bromide; potassium carbonate; In water; at 100℃; for 0.5h;Microwave irradiation; Green chemistry; | General procedure: In a 10-mL glass tube, (potassium) aromatic carboxylate (5.0 mmol), 1,4-dibromobutane (2.5 mmol), K2CO3 (1.0 mmol), TBAB (1.0 mmol), 1 mL H2O, and a magnetic stir bar were placed. The vessel was sealed with a septum and placed into the MW cavity. Microwave irradiation of 10 W was used, with the temperature was ramped from room temperature to 100 C. Once 100 C was reached, the reaction mixture was held at this temperature for 30 min. After cooling the mixture to room temperature, the reaction vessel was opened and the contents poured into a beaker with 50 mL water. The product was washed fully and filtered under vacuum. The product was recrystallized from 95% ethanol or purified by column chromatography on silica gel using petroleum-ethyl acetate (3:1 v/v) as the eluent, giving analytically pure products. Butane-1,4-diyl dibenzoate (3a) White crystal, mp (C) 82-83. 1H NMR (400 MHz, CDCl3): delta = 1.90-2.00 (m, 4H), 4.40 (m, 4H), 7.25-7.50 (m, 4H), 7.52-7.57 (m, 2H), 8.03-8.06 (m, 4H). 13C NMR (100 MHz, CDCl3): delta = 25.5, 64.4, 128.3, 129.5, 130.2, 132.8, 166.5. MS (m/z): Calculated for C18H18O4: 298.12, Found: 298. Anal. Calcd. For C18H18O4: C, 72.47; H, 6.08; Found: C, 72.46; H, 6.05; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With 18-crown-6 ether; In N,N-dimethyl-formamide; at 100℃; for 16h; | To a solution of (2R,3R,45, 5R)-2-(4-benzamidopyrrolo [2,1 -f] [1 ,2,4]triazin-7-yl)-2-cyano- 5-fluoro-5 - (iodomethyl)tetrahydrofuran-3,4-diyl dibenzoate (700 mg, 0.96 mmol) in N, Ndimethylformamide (70 mL) was added <strong>[582-25-2]potassium benzoate</strong> (767 mg, 4.79 mmol, 5.00 equiv) and 18-Crown-6 (507.5 mg, 1.92 mmol, 2.00 equiv). The resulting solution was stirred for 16 h at 100 C. The resulting solution was diluted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. After filtration, the resulting solution was concentrated under reduced pressure. Purification (silica gel column with ethyl acetate/petroleum ether (1:10-1:2)) afforded 350 mg (50%) of the title compound as a yellow solid. MS mlz: 726 [M+Hfb. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With 18-crown-6 ether; In N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere; | To a solution of (3aR,4R,6R,6a5)-4-(4-aminopyrrolo [2,1 -f] [1 ,2,4]triazin-7-yl)-6-fluoro-6- (iodomethyl)-2-methoxytetrahydrofuro[3 ,4-d] [1,31 dioxole-4-carbonitrile (1.0 g, 2.2 mmol) in DIVIF (100 mL) under inert atmosphere was added <strong>[582-25-2]BzOK</strong> (1.74 g, 11 mmol, 5.00 equiv), and 18-Crown-6 (1.15 g, 4.4 mmol, 2.00 equiv). The resulting solution was stirred for 16 hat 100C. The resulting solution was diluted with of EtOAc, washed with H20 and dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. Purification on silica gel column with EA/PE(l:l0-3:l) afforded 600 mg (61%) of the title compound as a yellow solid. MS mlz [M+H] (ESI): 456. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In acetonitrile; for 10h;Reflux; | The product IV (40.9 g, 0.1 mol) was dissolved in acetonitrile.Add 2 times the amount of benzoyl chloride (28.2 g, 0.2 mol), reflux reaction for 10 h, After the reaction was completed, the reaction solution was cooled to room temperature and diluted with water (2 L). Ethyl acetate was extracted three times (2 L × 3), and the ethyl acetate layer was combined. After washing three times with water, it was washed with saturated brine and evaporated to dryness under reduced pressure.The silica gel column ((petroleum ether / ethyl acetate = 20/1)) gave the product V (34.7 g), yield 74% |
Tags: 582-25-2 synthesis path| 582-25-2 SDS| 582-25-2 COA| 582-25-2 purity| 582-25-2 application| 582-25-2 NMR| 582-25-2 COA| 582-25-2 structure
Precautionary Statements-General | |
Code | Phrase |
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P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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