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CAS No. : | 93-14-1 | MDL No. : | MFCD00016873 |
Formula : | C10H14O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HSRJKNPTNIJEKV-UHFFFAOYSA-N |
M.W : | 198.22 | Pubchem ID : | 3516 |
Synonyms : |
Guaiacol glyceryl ether;Guaiphenesin;Scott Tussin;Methphenoxydiol;XL90;SL 90;NSC 62112;MY-301;Glycerol guaiacolate
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 51.36 |
TPSA : | 58.92 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.52 cm/s |
Log Po/w (iLOGP) : | 1.6 |
Log Po/w (XLOGP3) : | 1.39 |
Log Po/w (WLOGP) : | 0.43 |
Log Po/w (MLOGP) : | 0.37 |
Log Po/w (SILICOS-IT) : | 1.14 |
Consensus Log Po/w : | 0.98 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.93 |
Solubility : | 2.32 mg/ml ; 0.0117 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.23 |
Solubility : | 1.16 mg/ml ; 0.00588 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.98 |
Solubility : | 2.09 mg/ml ; 0.0105 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.34 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
72% | Stage #1: at 50℃; for 3 h; Reflux Stage #2: at 90℃; for 5 h; |
Equipped with a stirrer, a thermometer, a reflux condenser, a reaction vessel, 1.5mol sodium sulfite was added, the mass fraction of 20percent potassium chloride solution 300ml, controlling the stirring speed of 160 rpm, was slowly added guaiacol (2) 1.3mol, solution temperature rises to 50 , holding 3h, was added 3-amine 1,2-propanediol (3) 1.7mol, increasing the solution temperature 90 , maintained under stirring 5h, the temperature of the solution is reduced to 15 , allowed to stand for 25h after removing the aqueous layer delamination, the mass fraction of oil was added 200ml of 25percent solution of sodium bromide, mass fraction of 35percent oxalic acid solution was adjusted to maintain the pH at 7, after cooling the precipitated solid was suction filtered, washed with a solution of potassium nitrate, mass fraction washed with 70percent nitro methane in the mass fraction of 98percent propylene eye recrystallized to give crystals of 3- (o-methoxyphenoxy) -1,2-propanediol 185.33g, yield 72percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With calcined hydrotalcite In tetrahydrofuran at 120℃; for 4 h; Autoclave | In a typical reaction, autoclave reactor (details included in sup-porting information) was charged with guaiacol (0.0081 mol), gly-cidol (0.020 mol), tetrahydrofuran (THF) (10 mL) and 0.03 g mL−1(0.9 g) of the catalyst. The total organic phase volume was made to30 mL with THF. An initial sample was taken at the desired temperature. The reaction mixture was stirred with mechanical stirrer atthe desired speed, and samples were collected periodically. For control reaction, speed of agitation was 1000 rpm and temperature was 120°C at self-generated pressure. Reaction samples were analyzed by HPLC (details included in supporting information). Synthesis of guaifenesin (3-(2-methoxyphenoxy)propane-1,2-diol) andbyproduct (2-(2-methoxyphenoxy)propane-1,3-diol) from condensation reaction of guaiacol and glycidol is shown in Scheme 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 2 The procedure of Example 1 was employed but there was employed as catalyst 0.006 mole of powdered KOCN. Yield: 373 grams (94.2% of theory) guaiacol glycerine ether, as well as a residual content of 0.2 weight % free guaiacol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.15 - 97.7% | In water; at 35 - 50℃; for 1h;Product distribution / selectivity; | EXAMPLE 1 <strong>[93-14-1]Guaifenesin</strong> tannate was prepared as follows. In a 1-liter beaker were placed 340 g tannic acid (0.2 m), 163 g water and 39.6 g (0.2 m) of <strong>[93-14-1]guaifenesin</strong>. The mixture was heated to a temperature of 35-50 C. and was stirred for 1 hour. After cooling to room temperature, the entire reaction mixture was freeze dried at a reduced pressure of 200-100 milliTorr and a temperature of -50 to -40 C. for about 36 hours. At this point, the water which had been removed was condensed and its weight equaled about 160 g. The yield of <strong>[93-14-1]guaifenesin</strong> tannate was 365 g (96.15% of theory). EXAMPLE 2 [00036] Example 1 was repeated using a <strong>[93-14-1]guaifenesin</strong>: tannic acid molar ratio of 2: 1. In a 1-liter beaker were placed 340 g tannic acid (0.2 m), 180 g water and 79.3 g (0.4 m) of <strong>[93-14-1]guaifenesin</strong>. The mixture was heated to a temperature of 35-50 C. and was stirred for 1 hour. After cooling to room temperature, the entire reaction mixture was freeze dried at a reduced pressure of 200-100 milliTorr and a temperature of -50 to -40 C. for about 36 hours. At this point the water which had been removed was condensed and its weight equaled about 176 g. The yield of <strong>[93-14-1]guaifenesin</strong> tannate was 405 g (96.6% of theory). EXAMPLE 3 [00037] Example 1 was repeated using a <strong>[93-14-1]guaifenesin</strong>: tannic acid molar ratio of 5: 1. In a 1-liter beaker were placed 340 g tannic acid (0.2 m), 230 g water and 198.2 g (1 m) of <strong>[93-14-1]guaifenesin</strong>. The mixture was heated to a temperature of 35-50 C. and was stirred for 1 hour. After cooling to room temperature, the entire reaction mixture was freeze dried at a reduced pressure of 200-100 milliTorr and a temperature of -50 to -40 C. for about 36 hours. At this point, the water which had been removed was condensed and its weight equaled about 220 g. The yield of <strong>[93-14-1]guaifenesin</strong> tannate (which had a wet appearance) was 526 g (97.7% of theory). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.4 g (76%) | With pyridine; sodium hydrogencarbonate; In 1,4-dioxane; dichloromethane; water; | 1-[(2-Methoxyphenoxy)methyl]-1,2-ethanediol bissulfamate (ester) A solution of 10.4 g (0.06 mole) of sulfamic acid phenyl ester, 4.0 g (0.02 mole) of glyceryl guaiacolate and 2 ml of pyridine in 30 ml of p-dioxane was heated at reflux (104 C.) for 0.5 hr. The solution was cooled to 25 and 30 ml of methylene chloride was added. The solution was extracted with a dilute sodium bicarbonate solution. The sodium bicarbonate solution was prepared by dissolving 2 g of sodium bicarbonate in 25 ml water. After the bicarbonate extraction, the methylene chloride solution was washed with 25 ml of water then concentrated to a brown liquid. The addition of a mixture of 24 ml water and 24 ml isopropyl ether caused a white solid to precipitate. The solid was collected and dried to yield 5.4 g (76%) of title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.6 g (23%) | With triethylamine; In water; ethyl acetate; | EXAMPLE 48 Dimethylsulfamic acid 1-[(2-methoxyphenoxy)methyl]-1,2-propanediyl ester A mixture of 19.8 g (0.1 mole) of glyceryl guaiacolate, 114.9 g (0.8 mole) of dimethylsulfamoyl chloride (Aldrich) and 89.2 g (0.88 mole) of triethylamine was stirred at ambient temperature for 5 days. To this mixture was added an additional 58 g (0.4 mole) of dimethylsulfamoyl chloride (Aldrich) and 45 g (0.45 mole) of triethylamine and the mixture was stirred at ambient temperature for 2 days, treated with water and ethyl acetate (400 ml each). The layers were separated and the organic layer was washed with six 300 ml portions of water, dried over magnesium sulfate and the solvent evaporated under reduced pressure to yield a viscous oil. The oil was purified by chromatography (4.5*90 cm glass column; 500 g of silica gel; methylene chloride). Fractions containing title compound were combined and the solvent was evaporated under reduced pressure to give 10.3 g (25%) of an oil that solidified upon standing. The solid was recrystallized from methylene chloride-ethyl ether to give 9.6 g (23%) of white solid, mp 78-81 C. Analysis: Calculated for C14 H24 N2 O8 S2: C, 40.77; H, 5.87; N, 6.79. Found: C, 40.75; H, 5.98; N, 5.58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.3 g (58% recovery) | With triethylamine; benzyl alcohol;Pd-C; In acetonitrile; | EXAMPLE 59 Sulfamic acid 2-hydroxy-3-(2-methoxyphenoxy)propyl ester To a cold solution (5 C.) of 19.2 ml (0.22 mole) of chlorosulfonyl isocyanate in 180 ml of acetonitrile was added 23.8 g (0.22 mole) of benzyl alcohol (reaction mixture temperature, 5-8 C.). To this reaction mixture was added a solution of 39.6 g (0.2 mole) of glyceryl guaiacolate and 23.2 g (0.23 mole) of triethylamine in 180 ml of acetonitrile (reaction temperature, 5-12 C.). The reaction mixture was stirred for 3 hr, and the solids were removed by filtration. The filtrate was stirred with 1.5 g of 5% Pd-C for 1 hr, filtered, and the filtrate was divided into two equal fractions. Each fraction was stirred with 1.5 g of 5% Pd-C and hydrogenated. The catalyst was removed by filtration, and the filtrates were concentrated under reduced pressure to give 45 g and 42.3 g respectively. 13 C NMR showed the fractions to be identical. The two fractions were combined and were purified by chromatography (4.5*90 cm glass column; 550 g of silica gel; methylene chloride-acetone, 5:1). Fractions containing the desired component were combined and the solvents evaporated under reduced pressure to give 13.8 g of a viscous oil. The oil was triturated with methylene chloride and insolubles were removed by filtration. The filtrate was evaporated under reduced pressure to give 12.9 g of a viscous oil. A 4.0 g sample of this oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPAK 500 silica; methylene chloride-acetone, 10:1; flow rate 200 ml/min). Fractions containing the desired component were combined, and the solvents evaporated under reduced pressure to give 2.3 g (58% recovery) of the title compound as a brown gum containing a trace of methylene chloride. Analysis: Calculated for C10 H15 NO6 S: C, 43.32; H, 5.45; N, 5.05. Found: C, 42.60; H, 5.48; N, 4.96. |
2.3 g (58% recovery) | With triethylamine; benzyl alcohol;Pd-C; In acetonitrile; | EXAMPLE 68 3-(2-Methoxyphenoxy)-1,2-propanediol 1-sulfamate To a cold solution (5 C.) of 19.2 ml (0.22 mole) of chlorosulfonyl isocyanate in 180 ml of acetonitrile was added 23.8 g (0.22 mole) of benzyl alcohol (reaction mixture temperature, 5-8 C.). To this reaction mixture was added a solution of 39.6 g (0.2 mole) of glyceryl guaiacolate and 23.2 g (0.23 mole) of triethylamine in 180 ml of acetonitrile (reaction temperature, 5-12 C.). The reaction mixture was stirred for 3 hr, and the solids were removed by filtration. The filtrate was stirred with 1.5 g of 5% Pd-C for 1 hr, filtered, and the filtrate was divided into two equal fractions. Each fraction was stirred with 1.5 g of 5% Pd-C and hydrogenated. The catalyst was removed by filtration, and the filtrates were concentrated under reduced pressure to give 45 g and 42.3 g respectively. 13 C NMR showed the fractions to be identical. The two fractions were combined and were purified by chromatography (4.5*90 cm glass column; 550 g of silica gel; methylene chloride-acetone, 5:1). Fractions containing the desired component were combined and the solvents evaporated under reduced pressure to give 13.8 g of a viscous oil. The oil was triturated with methylene chloride and insolubles were removed by filtration. The filtrate was evaporated under reduced pressure to give 12.9 g of a viscous oil. A 4.0 g sample of this oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPAK 500 silica; methylene chloride-acetone, 10:1; flow rate 200 ml/min). Fractions containing the desired component were combined, and the solvents evaporated under reduced pressure to give 2.3 g (58% recovery) of the title compound as a brown gum containing a trace of methylene chloride. Analysis: Calculated for C10 H15 NO6 S: C, 43.32; H, 5.45; N, 5.05; Found: C, 42.60; H, 5.48; N, 4.96. |
2.3 g (58% recovery) | With triethylamine; benzyl alcohol;Pd-C; In acetonitrile; | EXAMPLE 40 Sulfamic acid 2-hydroxy-3-(2-methoxyphenoxy)propyl ester To a cold solution (5 C.) of 19.2 ml (0.22 mole) of chlorosulfonyl isocyanate in 180 ml of acetonitrile was added 23.8 g (0.22 mole) of benzyl alcohol (reaction mixture temperature, 5-8 C.). To this reaction mixture was added a solution of 39.6 g (0.2 mole) of glyceryl guaiacolate and 23.2 g (0.23 mole) of triethylamine in 180 ml of acetonitrile (reaction temperature, 5-12 C.). The reaction mixture was stirred for 3 hr, and the solids were removed by filtration. The filtrate was stirred with 1.5 g of 5% Pd-C for 1 hr, filtered, and the filtrate was divided into two equal fractions. Each fraction was stirred with 1.5 g of 5% Pd-C and hydrogenated. The catalyst was removed by filtration, and the filtrates were concentrated under under reduced pressure to give 45 g and 42.3 g respectively. 13 C NMR showed the fractions to be identical. The two fractions were combined and were purified by chromatography (4.5*90 cm glass column; 550 g of silica gel; methylene chloride-acetone, 5:1). Fractions containing the desired component were combined and the solvents evaporated under reduced pressure to give 13.8 g of a viscous oil. The oil was triturated with methylene chloride and insolubles were removed by filtration. The filtrate was evaporated under reduced pressure to give 12.9 g of a viscous oil. A 4.0 g sample of this oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPAK 500 silica; methylene chloride-acetone, 10:1; flow rate 200 ml/min). Fractions containing the desired component were combined, and the solvents evaporated under reduced pressure to give 2.3 g (58% recovery) of the title compound as a brown gum containing a trace of methylene chloride. Analysis: Calculated for C10 H15 NO6 S: C, 43.32; H, 5.45; N, 5.05. Found: C, 42.60; H, 5.48; N, 4.96. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13.9 g (37%) | With pyridine; In dichloromethane; | EXAMPLE 58 Methylsulfamic acid 2-hydroxy-3-(2-methoxyphenoxy)propyl ester A solution of 26.5 g (0.13 mole) of glycerol guaiacolate in 100 ml of methylene chloride and 10.8 ml (0.13 mole) of pyridine was added in a thin stream to a stirred solution of 17.1 g (0.13 mole) of N-methylsulfamoyl chloride (Preparation 22) in 70 ml of methylene chloride, and the reaction mixture was stirred at ambient temperature for 2 hr. The reaction mixture was treated with 150 ml of water, the layers were separated, and the organic layer was washed successively with a 200 ml portion of 2N hydrochloric acid solution, four 200 ml portions of water, dried (magnesium sulfate), and the solvent was evaporated under reduced pressure to yield a viscous oil. The oil was purified by preparative high pressure liquid chromatography. Fractions containing the desired product were combined and the solvents evaporated under reduced pressure to give 13.9 g (37%) of the title compound as a yellow gum. Analysis: Calculated for C11 H17 NO6 S: C, 45.35; H, 5.88; N, 4.81. Found: C, 44.99; H, 5.95; N, 4.78. |
13.9 g (37%) | With pyridine; In dichloromethane; | EXAMPLE 67 Methylsulfamic acid 2-hydroxy-3-(2-methoxyphenoxy)propyl ester A solution of 26.5 g (0.13 mole) of glycerol guaiacolate in 100 ml of methylene chloride and 10.8 ml (0.13 mole) of pyridine was added in a thin stream to a stirred solution of 17.1 g (0.13 mole) of N-methylsulfamoyl chloride (Preparation 24) in 70 ml of methylene chloride, and the reaction mixture was stirred at ambient temperature for 2 hr. The reaction mixture was treated with 150 ml of water, the layers were separated, and the organic layer was washed successively with a 200 ml portion of 2N hydrochloric acid solution, four 200 ml portions of water, dried (magnesium sulfate), and the solvent was evaporated under reduced pressure to yield a viscous oil. The oil was purified by preparative high pressure liquid chromatography. Fractions containing the desired product were combined and the solvents evaporated under reduced pressure to give 13.9 g (37%) of the title compound as a yellow gum. Analysis: Calculated for C11 H17 NO6 S: C, 45.35; H, 5.88; N, 4.81; Found: C, 44.99; H, 5.95; N, 4.78. |
13.9 g (37%) | With pyridine; In dichloromethane; | EXAMPLE 39 Methylsulfamic acid 2-hydroxy-3-(2-methoxyphenoxy)propyl ester A solution of 26.5 g (0.13 mole) of glycerol guaiacolate in 100 ml of methylene chloride and 10.8 ml (0.13 mole) of pyridine was added in a thin stream to a stirred solution of 17.1 g (0.13 mole) of N-methylsulfamoyl chloride in 70 ml of methylene chloride, and the reaction mixture was stirred at ambient temperature for 2 hr. The reaction mixture was treated with 150 ml of water, the layers were separated, and the organic layer was washed successively with a 200 ml portion of 2N hydrochloric acid solution, four 200 ml portions of water, dried (magnesium sulfate), and the solvent was evaporated under reduced pressure to yield a viscous oil. The oil was purified by preparative high pressure liquid chromatography. Fractions containing the desired product were combined and the solvents evaporated under reduced pressure to give 13.9 g (37%) of the title compound as a yellow gum. Analysis: Calculated for C11 H17 NO6 S: C, 45.35; H, 5.88; N, 4.81. Found: C, 44.99; H, 5.95; N, 4.78. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; dichloromethane; ethyl acetate; | EXAMPLE 43 Methylsulfamic acid 1-chloro-3-(2-methoxyphenoxy)-2-propyl ester A solution of 109.3 g (0.55 mole) of glyceryl guaiacolate in 177 ml (2.20 moles) of pyridine and 700 ml methylene chloride was added to a solution of 283 g (2.20 moles) of methylaminosulfonyl chloride in 700 ml of methylene chloride. The addition was made over one hour at 15-22 C. The solution was stirred at 23 C. for two hours then washed with 3*500 ml water. The methylene chloride solution was dried over type 3A molecular sieves. The mixture was filtered and the filtrate diluted with 140 ml of ethyl acetate. The solution was chromatographed on 2 kg of silica gel using 10% ethyl acetate:methylene chloride solution as eluent. The first 3*750 ml fractions were combined and concentrated to 77.3 g of brown oil. The oil was redissolved in 400 ml of 10% ethyl acetate:methylene chloride solution and chromatographed on 1.5 kg of silica gel. A total of 9*250 ml fractions were collected that showed only one spot on TLC. The fractions were combined and concentrated to 20.6 g of oil which crystallized on standing. The 20.6 g was recrystallized from 20 ml of isopropyl alcohol to give 6.9 g of white solid, mp 84-85 C. The compound was characterized by 1 H NMR, 13 C NMR and C-I mass spec. Analysis: Calculated for C11 H16 ClNO5 S: C, 42.65; H, 5.21; N, 4.52. Found: C, 42.32; H, 5.25; N, 4.61. | |
In pyridine; dichloromethane; ethyl acetate; | EXAMPLE 51 1-Chloro-3-(2-methoxyphenoxy)-2-propanol methylsulfamate ester A solution of 109.3 g (0.55 mole) of glyceryl guaiacolate in 177 ml (2.20 moles) of pyridine and 700 ml methylene chloride was added to a solution of 283 g (2.20 moles) of methylaminosulfonyl chloride in 700 ml of methylene chloride. The addition was made over one hour at 15-22 C. The solution was stirred at 23 C. for two hours then washed with 3*500 ml water. The methylene chloride solution was dried over type 3A molecular sieves. The mixture was filtered and the filtrate diluted with 140 ml of ethyl acetate. the solution was chromatographed on 2 kg of silica gel using 10% ethyl acetate: methylene chloride solution as eluent. The first 3*750 ml fractions were combined and concentrated to 77.3 g of brown oil. The oil was redissolved in 400 ml of 10% ethyl acetate: methylene chloride solution and chromatographed on 1.5 kg of silica gel. A total of 9*250 ml fractions were collected that showed only one spot on TLC. The fractions were combined and concentrated to 20.6 g of oil which crystallized on standing. The 20.6 g was recrystallized from 20 ml of isopropyl alcohol to give 6.9 g of white solid, mp 84-85 C. The compound was characterized by 1 H NMR, 13 C NMR and C-I mass spec. Analysis: Calculated for C11 H16 ClNO5 S: C, 42.65; H, 5.21; N, 4.52; Found: C, 42.32; H, 5.25; N, 4.61. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; dichloromethane; sulfuric acid; water; benzene; | b. Preparation of the title compound Into a stirred solution of the 20.1 g (0.10 mole) of the isopropyl ester of N-chlorosulfonyl carbamic acid in 30 ml of methylene chloride, cooled by an ice bath was poured a suspension of 8 g (0.04 mole) of 3-(2-methoxyphenoxy)-1,2-propanediol (which is glyceryl guaiacolate) in a 8.1 ml (0.1 mole) of pyridine. Exothermic reaction caused gentle boiling. The ice bath was removed after the addition and stirring was continued for 2 hr. Water, 80 ml, was added to the reaction mixture and stirring continued for 20 min additional time. The organic layer was separated and washed twice more with water. The organic layer was extracted three times with sodium bicarbonate solution. The combined bicarbonate solution containing the product was stirred with methylene chloride in an ice bath with adding sulfuric acid to acidifying the mixture. The layers were separated and the aqueous layer was extracted once with methylene chloride. The methylene chloride layers were combined, washed with water, dried over sodium sulfate, filtered and concentrated to give 23 g of an oil. 1 H NMR analysis showed title compound with a small contamination of methylene chloride. A 10 g portion of the oil in benzene was freeze-dried in an attempt to obtain solid; however an oil resulted. 1 H NMR analysis showed methylene chloride had been exchanged for benzene in amount of about 0.25 mole benzene per mole of title compound. | |
In pyridine; dichloromethane; sulfuric acid; water; benzene; | b. Preparation of the title compound. Into a stirred solution of the 20.1 g (0.10 mole) of the isopropyl ester of N-chlorosulfonyl carbamic acid in 30 ml of methylene chloride, cooled by an ice bath was poured a suspension of 8 g (0.04 mole) of 3-(2-methoxyphenoxy)-1,2-propanediol (which is glyceryl guaiacolate) in a 8.1 ml (0.1 mole) of pyridine. Exothermic reaction cause gentle boiling. The ice bath was removed after the addition and stirring was continued for 2 hr. Water, 80 ml, was added to the reaction mixture and stirring continued for 20 min additional time. The organic layer was separated and washed twice more with water. The organic layer was extracted three times with sodium bicarbonate solution. The combined bicarbonate solution containing the product was stirred with methylene chloride in an ice bath with adding sulfuric acid to acidifying the mixture. The layers were separated and the aqueous layer was extracted once with methylene chloride. The methylene chloride layers were combined, washed with water, dried over sodium sulfate, filtered and concentrated to give 23 g of an oil. 1 H NMR analysis showed title compound with a small contamination of methylene chloride. A 10 g portion of the oil in benzene was freeze-dried in an attempt to obtain solid; however an oil resulted. 1 H NMR analysis showed methylene chloride had been exchanged for benzene in amount of about 0.25 mole benzene per mole of title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20.2 g (49%) | With pyridine; hydrogenchloride; In dichloromethane; | EXAMPLE 72 Ethylsulfamic acid 2-[[(ethylamino)sulfonyl]oxy]-3-(2-methoxyphenoxy)propyl ester A solution of 19.8 g (0.1 mole) of glyceryl guaiacolate in 100 ml of methylene chloride and 21.6 ml (0.26 mole) of pyridine was added in a thin stream to a stirred solution of 37.3 g (0.26 mole) of ethylsulfamoyl chloride (Preparation 25) in 150 ml of methylene chloride, and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was treated with 150 ml of 2N hydrochloric acid solution, and the layers were separated. The organic layer was washed with 150 ml of 2N hydrochloric acid solution, twice with 150 ml portions of water, dried (magnesium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by chromatography (4.5*90 cm glass column; 500 g of silica gel; methylene chloride-acetone, 25:1). Fractions containing the product were combined, and the solvents wre evaporated under reduced pressure to give 20.2 g (49%) of the title compound as a light-yellow, viscous oil containing a trace of methylene chloride. Analysis: Calculated for C14 H24 N2 O8 S2: C, 40.77; H, 5.86; N, 6.79: Found: C, 40.21; H, 5.94; N, 6.77. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.6 g (23%) | With triethylamine; In water; ethyl acetate; | EXAMPLE 33 Dimethylsulfamic acid 3-(2-methoxyphenoxy)-1,2-propanediyl ester A mixture of 19.8 g (0.1 mole) of glyceryl guaiacolate, 114.9 g (0.8 mole) of dimethylsulfamoyl chloride (Aldrich) and 89.2 g (0.88 mole) of triethylamine was stirred at ambient temperature for 5 days. To this mixture was added an additional 58 g (0.4 mole) of dimethylsulfamoyl chloride (Aldrich) and 45 g (0.45 mole) of triethylamine and the mixture was stirred at ambient temperature for 2 days, treated with water and ethyl acetate (400 ml each). The layers were separated and the organic layer was washed with six 300 ml portions of water, dried over magnesium sulfate and the solvent evaporated under reduced pressure to yield a viscous oil. The oil was purified by chromatography (4.5*90 cm glass column; 500 g of silica gel; methylene chloride). Fractions containing title compound were combined and the solvent was evaporated under reduced pressure to give 10.3 g (25%) of an oil that solidified upon standing. The solid was recrystallized from methylene chloride-ethyl ether to give 9.6 g (23%) of white solid, mp 78-81 C. Analysis: Calculated for C14 H24 N2 O8 S2: C, 40.77; H, 5.87; N, 6.79. Found: C, 40.75; H, 5.98; N, 6.58. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20.2 g (49%) | With pyridine; hydrogenchloride; In dichloromethane; | EXAMPLE 44 Ethylsulfamic acid 3-(2-methoxyphenoxy)propyl ester A solution of 19.8 g (0.1 mole) of glyceryl guaiacolate in 100 ml of methylene chloride and 21.6 ml (0.26 mole) of pyridine was added in a thin stream to a stirred solution of 37.3 g (0.26 mole) of ethysulfamoyl chloride (prepared using procedure of Example 2, pt. a) in 150 ml of methylene chloride, and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was treated with 150 ml of 2N hydrochloric acid solution, and the layers were separated. The organic layer was washed with 150 ml of 2N hydrochloric acid solution, twice with 150 ml portions of water, dried (magnesium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by chromatography (4.5*90 cm glass column; 500 g of silica gel; methylene chloride-acetone, 25:1). Fractions containing the product were combined, and the solvents wre evaporated under reduced pressure to give 20.2 g (49%) of the title compound as a light-yellow, viscous oil containing a trace of methylene chloride. Analysis: Calculated for C14 H24 N2 O8 S2: C, 40.77; H, 5.86; N, 6.79. Found: C, 40.21; H, 5.94; N, 6.77. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; benzene; | EXAMPLE 7 A solution of <strong>[93-14-1]3-(2-methoxy-phenoxy)-propane-1,2-diol</strong> (4.7 g) in pyridine, cooled at 5-10C, is treated under stirring with a solution of p-toluensulphonylchloride (4.5 g) in benzene (70 ml). The reaction mixture is stirred overnight at room temperature, then it is washed with 2N HCl (3 x 100 ml) and with water, dried on Na2SO4 and evaporated to dryness in vacuum. The oily residue is purified by column chromatography (silica gel - 230-400 mesh hexane / AcOEt = 3 / 1) to yield 5 g of 3-(2-methoxy-phenoxy)-2-hydroxy-1-propyl p-toluensulphonate (oil, NMR (-CDCl3): = 2,4 2H (s) CH 3SO2; = 3,75-4,4 5H (m) OCH 3 + OCH 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; silver nitrate; In tetrahydrofuran; at 0 - 20℃; for 14h; | The compound : EPO <DP n="44"/>1 , 2-di-0-nitro-3 (o-methoxyphenoxy) -propanediolwas prepared according to the following procedure.<strong>[93-14-1]Guaifenesin</strong> (1.982 g, 10 mmol) was suspended in tetra- hydrofuran (THF) (50 ml) and silver nitrate (AgNO3) (6.8 g, 40 mmol) was added all at once. After dropwise addition of freshly distilled thionyl chloride SOCl2 (d = 1.631; 2.38 g, 20 mmol, 1.46 ml) in ice-cold conditions, the mixture was stirred for 14 hours at room temperature. Pure water (H2O) (25 ml) was added to the reaction system and the mixture was extracted with acetyl -acetate (AcOEt) (20 ml x 3) . The combined organic layers were washed with saturated sodium biocarbonate (NaHCO3) (10 ml x 3) , then with distilled water (10 ml x 3) . The extract was dried with anhydrous magnesium sulphate (MgSO4) . The solvent was evaporated and the product was dried with silica gel using a Rotary Evaporator. The product was purified by silica gel (Aldrich No.227196, Merck grade 9385, 230-400 mesh, 60A) column chromatography. EPO <DP n="45"/>This procedure may be depicted asReagents: AgNO3, SOCl2 Solvent: THF, AcOEtFlash Chromatography:A chromatography column (Kontes 30 x 500 mm) was packed with silica gel to 350 mm length and equilibrated with acetyl- acetate/hexane mixture (AcOEt/Hexane) (1:3, volume-to-volume) . The separation and elution were performed with a slight air pressure on the top of the same solvents (AcOEt/Hexane at ratio of 1/3) ; the elution rate was controlled at one drop per second. Forty fractions were collected from the column at 25 ml per fraction following elution of the first 200 ml. In each fraction, bands were identified using fluorescent thin layer chromatography to examining the eluted compounds .The compound was identified using the following techniques:1) The compound was characterized by 1H NMR (Figure 9) and 1X3J/C NMR (Figure 10) . The NMR peaks were assigned by NMR-COSY (Correlation SpectroscopY, a 2 -dimensional H-H correlation NMR technique; Figure 11) and NMR-HMQC (Heteronuclear Multiple Quantum Correlation spectroscopy, a 2 -dimensional C-H correlation NMR technique; Figure 12) , EPO <DP n="46"/>2) HPLC and LC-MS were used to obtain the molecular mass of the compound (Figures 13 and 14) ,3) Ultraviolet spectrophotometry (Figure 15b), together with a comparison with <strong>[93-14-1]guaifenesin</strong> (Figure 15a) , and4) Infrared spectrophotometry together with a comparison with <strong>[93-14-1]guaifenesin</strong> (Figure 16) . MyoNovin is the upper tracing, and <strong>[93-14-1]guaifenesin</strong> the lower.The target compound has a molecular mass of 288.0675 g/mole and is identified as 1- (2 , 3-bis-nitrooxy-propoxy) -2-methoxy-benzene or 1 , 2-di-0-nitro-3 (o-methoxyphenoxy) -propanediol . We have named it 'MyoNovin' . | |
With thionyl chloride; silver nitrate; In tetrahydrofuran; at 20℃; for 14h; | <strong>[93-14-1]Guaifenesin</strong> (1.982 g, 10 mmol) was suspended in tetrahydrofuran (THF) (50 ml), Add silver nitrate (AgNO3) (6.8 g, 40 mmol) in one portion. Freshly added thionyl chloride SOCl2 (d = 1.631; 2.38 g, 20 mmol, 1.46 ml) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 14 hours. Pure water (H2O) (25 ml) was added to the reaction system, and extracted with ethyl acetate (AcOEt) (20 ml × 3). The combined organic layers were washed with saturated sodium bicarbonate (NaHCO3) (10 ml x 3), and then washed with distilled water (10 ml x 3). The extract was dried over anhydrous magnesium sulfate (MgSO4). The solvent was evaporated and the product was dried on silica gel using a rotary evaporator. The product was purified by silica gel (Aldrich 227196, Merck grade 9385, 230-400 mesh, 60A) column chromatography. Flash chromatography: The column (Kontes 30 x 500 mm) was packed with silica gel to a length of 350 mm and equilibrated with an ethyl acetate / hexane mixture (AcOEt / hexane) (1: 3, volume-volume).Separate and elute with a slight pressure on top of the same solvent (AcOEt / hexane, ratio 1/3); the elution rate is controlled to one drop per second.After eluting the first 200 ml, 40 fractions were collected from the column at 25 ml each. In each fraction, bands were identified using fluorescence thin layer chromatography to check the eluted compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
C. Regioselective diol mono-tosylation using the generic acetal compound 3a; The generic acetal compound 3a was used to perform the mono-tosylation reaction according Scheme 2 for a series of compounds. In short, a mixture of the corresponding diol, stannylene acetal 3a, iPr2NEt and TsCl in various amounts was stirred at room temperature for 16 hours. Hydrochloric acid IN (1.5 eq.) was added and the mixture was stirred vigorously. The organic phase was filtered over sodium sulfate and used further as such in the next step.The results are shown in Table 2. From the Table 2 can be seen that the amount of compound 3a in the catalyzed mono-tosylation reaction could be lowered down to as low as 0.001 mol%. This presents a major improvement over the prior art preparation methods and allows for the production of API's with very low Sn concentrations. <n="10"/>Table 2Substrates 1 to 4: % conversion and selectivity is based on HPLC area%.Substrates 5 and 6: % conversion and selectivity is based on GC area%.* The GC chromatogram didn't show any ditosylation or starting material, analysis with HPLC showed some ditosylation. | ||
C. Regioselective diol mono-tosylation using the generic acetal compound 3a; The generic acetal compound 3a was used to perform the mono-tosylation reaction according Scheme 2 for a series of compounds. In short, a mixture of the corresponding diol, stannylene acetal 3a, iPr2NEt and TsCl in various amounts was stirred at room temperature for 16 hours. Hydrochloric acid IN (1.5 eq.) was added and the mixture was stirred vigorously. The organic phase was filtered over sodium sulfate and used further as such in the next step.The results are shown in Table 2. From the Table 2 can be seen that the amount of compound 3a in the catalyzed mono-tosylation reaction could be lowered down to as low as 0.001 mol%. This presents a major improvement over the prior art preparation methods and allows for the production of API's with very low Sn concentrations. <n="10"/>Table 2Substrates 1 to 4: % conversion and selectivity is based on HPLC area%.Substrates 5 and 6: % conversion and selectivity is based on GC area%.* The GC chromatogram didn't show any ditosylation or starting material, analysis with HPLC showed some ditosylation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In vitro, 4-phenylbutane-1,2-diol(26.3 mg, 0.158 mmol), and was dissolved in Kanto Chemical Co.toluene (790mul), to this solution, manufactured by Tokyo Chemical Industry Co.,Ltd. TEMPO " 2,2,6,6-tetramethylpiperidine 1-oxyl free radical"(trade name) (1.24mg, 7.92mumol) and, pH 6.8 for 1M- phosphate buffer and(565mul) was added, at 25C the mixture was stirred for 5 minutes .Then, while stirring the mixture, 80% sodium chlorite (53.7mg, 0.475 mmol) and an aqueous solution dissolved in water (200 mul), an aqueous solution of sodium hypochlorite (7.92mumol) (0 .168M, and 47.1mul) and,simultaneously, was added dropwise over 1 minute.Thereafter, the reaction system as a 25 C., was carriedout for 4 hours the reaction was continued stirring. Then, a 0.1M- phosphatebuffer pH 2.1 (3 ml), and sodium chloride was added to complete the oxidationreaction.Then, extracted with ethyl acetate, to recover an organiclayer containing the alpha- hydroxy carboxylic acids of interest. Then, washing theorganic layer with saturated brine, dried over anhydrous magnesium sulfate,then, under reduced pressure, and Datsu to give the crude product. This crudeproduct, n- octyl ether was subjected to NMR measurement as a standardsubstance, and the target product of 2-hydroxy-4-phenylbutyric acid (95%), aby-product, 3-phenylpropionic acid it was found that (4.7%) and hasbeen included (see Figure 1 and Table 1). Therefore, the crude product waspurified by silica gel column chromatography (SO3H), to give2-hydroxy-4-phenylbutyric acid shown in the following (26.9mg). The yield was 86%. Instead of 4-phenylbutane-1,2-diol, using a 3-(O-methoxyphenoxy) 1,2-propanediol shown below, the temperature of the reactionsystem as a 50 C., the reaction time was 24 hours Otherwise, in the samemanner as in example 1 to give 2-hydroxy-3- (2-methoxyphenoxy) propionic acidare shown below. Further, the yield of the purified 2-hydroxy-3-(2-methoxyphenoxy) propionic acid was 73%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - 0℃; for 1h; | (0 07} Step-5: Synthesis of compound 9: (00108} To a solution of compound 3 (1.0 mmol) in dry DCM (1.8 ml) was added N, - diisopropylethylamine (2.0 mmoi) at -0C, followed by drop wise addition of compound 8 (1.1 mmol ) at the same temperature and the reactio mixture was allowed to stir for 1 h at 0C. On completion of the reaction (monitored by TLC), the reaction mixture the solvent was evaporated and the crude was purified t ough column to get compound 9. | |
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - 0℃; for 1h; | To a solution of compound 3 (1.0 mmol) in dry DCM (1.8 ml) was added N, N-diisopropylethylamine (2.0 mmol) at -10 C., followed by drop wise addition of compound 8 (1.1 mmol) at the same temperature and the reaction mixture was allowed to stir for 1 h at 0 C. On completion of the reaction (monitored by TLC), the reaction mixture the solvent was evaporated and the crude was purified through column to get compound 9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
{0097] Step3: Synthesis of compound 7:[00981 Compound 5 (10 m.mol) is suspended in DC. and cooled 0 C, and added thionyl chloride (30 mmol) drop wise. The reaction. mixture is heated at 50 C for I h and then cooled to Ct added compound 3 drop wise and heated the reaction mixture at..S0 C foi 8 h M?tcr (omplcnon of thc Raction the so]atilc art iemoxd in xacuo Thc ftslduc was taken in water and extracted wuh 13CM (2X50 niI) The 13CM layer was dried over Na:2S04, evaporated and the crude product was crystallized using appropriate solvent get to get compound 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium 10% on activated carbon; oxygen; sodium acetate; potassium iodide; In 1,2-dimethoxyethane; at 100℃; under 10343.2 Torr; for 3h;Autoclave; Inert atmosphere; | General procedure: In a 100 mL stainless steel autoclave, diol (5mmol), catalyst (10 % Pd/C, 0.5 mol %), KI (0.09 mmol), base (1.25 mmol),solvent (10 mL) were added. The autoclave was closed, flushed with nitrogen,pressurized with O2 (33 psi) and CO (167 psi) and reaction mixturewas stirred with a mechanical starrer (520 rpm) at desired temperature forappropriate time period. After completion of reaction, the reactor was thencooled to room temperature, degassed carefully and opened. The reaction mixturewas filtered and the solvent was evaporated under vacuum. The reaction mixturewas analyzed by GC analysis (Perkin-Elmer, Clarus 400) equipped with a flameionization detector (FID) and a capillary column (Elite-1, 30 m × 0.32 mm ×0.25 mum). Purification of residue was carried out by column chromatography(silica gel 100-200 mesh, petroleum ether/ethyl acetate) to afford thecorresponding products in good to excellent yield. The prepared compounds werecharacterized by 1H NMR (Varian 200 MHz NMR Spectrometer), 13CNMR spectra (50 MHz) and GC-MS (Shimadzu GC-MS QP 2010) (Rtx-17, 30 m × 25mmID,film thickness 0.25 mum df) (column flow- 2 mL/min, 80 C to 240 C at 10/min.rise.) which were consistent with those reported in the literature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equalamounts (0.02 mol) of hot saturated ethanolic solution of the GFSligand with the same ratio of metal chloride. The mixture wasrefluxed for 3 h. The resulting complexes were filtered and washedseveral times with hot ethanol until the filtrates become clear. Thesolid complexes then dried in desiccator over anhydrous calciumchloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 0 - 50℃; for 8h; | Compound 5 (10 mmol) is suspended in DCM and cooled to 0 C., and added thionyl chloride (30 mmol) drop wise. The reaction mixture is heated at 50 C. for 1 h and then cooled to 0 C. added compound 3 drop wise and heated the reaction mixture at 50 C. for 8 h. After completion of the reaction, the volatiles are removed in vacuo. The residue was taken in water and extracted with DCM (2×50 ml). The DCM layer was dried over Na2SO4, evaporated and the crude product was crystallized using appropriate solvent to get compound 7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equal amounts (0.02 mol) of hot saturated ethanolic solution of the GFS and 2-aminoacetic acid (HGly) with the same ratio of metal chloride (1 M: 1 GFS: 1 Gly molar ratio). The mixture was refluxed for three hours. The resulting complexes were filtered and washed several times with hot ethanol until the filtrates become clear. The solid complexes then dried in desicator over anhydrous calcium chloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equal amounts (0.02 mol) of hot saturated ethanolic solution of the GFS and 2-aminoacetic acid (HGly) with the same ratio of metal chloride (1 M: 1 GFS: 1 Gly molar ratio). The mixture was refluxed for three hours. The resulting complexes were filtered and washed several times with hot ethanol until the filtrates become clear. The solid complexes then dried in desicator over anhydrous calcium chloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equal amounts (0.02 mol) of hot saturated ethanolic solution of the GFS and 2-aminoacetic acid (HGly) with the same ratio of metal chloride (1 M: 1 GFS: 1 Gly molar ratio). The mixture was refluxed for three hours. The resulting complexes were filtered and washed several times with hot ethanol until the filtrates become clear. The solid complexes then dried in desicator over anhydrous calcium chloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equal amounts (0.02 mol) of hot saturated ethanolic solution of the GFS and 2-aminoacetic acid (HGly) with the same ratio of metal chloride (1 M: 1 GFS: 1 Gly molar ratio). The mixture was refluxed for three hours. The resulting complexes were filtered and washed several times with hot ethanol until the filtrates become clear. The solid complexes then dried in desicator over anhydrous calcium chloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equal amounts (0.02 mol) of hot saturated ethanolic solution of the GFS and 2-aminoacetic acid (HGly) with the same ratio of metal chloride (1 M: 1 GFS: 1 Gly molar ratio). The mixture was refluxed for three hours. The resulting complexes were filtered and washed several times with hot ethanol until the filtrates become clear. The solid complexes then dried in desicator over anhydrous calcium chloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equal amounts (0.02 mol) of hot saturated ethanolic solution of the GFS and 2-aminoacetic acid (HGly) with the same ratio of metal chloride (1 M: 1 GFS: 1 Gly molar ratio). The mixture was refluxed for three hours. The resulting complexes were filtered and washed several times with hot ethanol until the filtrates become clear. The solid complexes then dried in desicator over anhydrous calcium chloride. The yield ranged from 60% to 94%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In ethanol; for 3h;Reflux; | General procedure: The present metal complexes were prepared by mixing equal amounts (0.02 mol) of hot saturated ethanolic solution of the GFS and 2-aminoacetic acid (HGly) with the same ratio of metal chloride (1 M: 1 GFS: 1 Gly molar ratio). The mixture was refluxed for three hours. The resulting complexes were filtered and washed several times with hot ethanol until the filtrates become clear. The solid complexes then dried in desicator over anhydrous calcium chloride. The yield ranged from 60% to 94%. |
Tags: 93-14-1 synthesis path| 93-14-1 SDS| 93-14-1 COA| 93-14-1 purity| 93-14-1 application| 93-14-1 NMR| 93-14-1 COA| 93-14-1 structure
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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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