* 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.
With trichlorophosphate; In chloroform; at 90℃; for 9h;
1) 346 g (1.5 mol) of sodium 2-naphthalenesulfonate and 770 g (5 mol) of phosphorus oxytrichloride were successively added to 2.25 mol of chloroform to obtain a reaction solution a;2) The reaction liquid a obtained in the step 1) is reacted at a temperature of 90 C for 9 hours to obtain a mixed liquid b;3) the step 2) obtained by the mixture b continued to steam out the excess of phosphorus oxychloride and chloroform, followed by washing, filtration, vacuum distillation, in 2 - naphthalene sulfonyl chloride.It was calculated that the product yield of the 2-naphthalenesulfonyl chloride was 95.8%.
methyl (+)-(S)-α-(o-chlorophenyl)-6,7-dihydrothieno[3,2-a]pyridine-5(4H)acetate 2-naphthalenesulfonate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In methanol; water; at 20℃;Product distribution / selectivity;
EXAMPLE 10 Clopidogrel Napsylate, Form A 2.5 g sodium-2-naphthylsulfonate are dissolved in 60 ml of water. Suspended material is separated by filtration. 30 ml methanol and 2.9 g Clopidogrel hydrobromide are then added. The solution obtained is vigorously stirred and put under slight vacuum and kept at room temperature until about 50% by weight of the solvent has slowly evaporated. The white solid thus formed is isolated by vacuum filtration, washed with water and dried under vacuum until constant weight. 3 g Clopidogrel napsylate of Form A are obtained.
methyl (+)-(S)-α-(o-chlorophenyl)-6,7-dihydrothieno[3,2-a]pyridine-5(4H)acetate 2-naphthalenesulfonate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
52.5 g sodium-2-naphthylsulfonate are dissolved in 430 ml dematerialized water under heating at about 75 C. A solution of 50 g Clopidogrel hydrogen sulfate in 200 ml water is added to the solution. The resulting mixture is cooled to room temperature and the upper oily phase is separated. The separated oil is dissolved in 230 g isopropanol. The obtained solution is dried with magnesium sulfate and diluted with 250 g diisopropylether. The solution is inoculated at a temperature of about 60 C. with Clopidogrel napsylate and stirred over night whilst cooling to room temperature. The solid material is isolated by vacuum filtration, washed with diisopropylether and dried under vacuum. 37 g Clopidogrel napsylate of Form A are obtained with the following properties: HPLC content of Clopidogrel napsylate: 100% DSC: endothermic maximum: 149 C. IR (KBr pressed mass) [cm-1 at % transmission]: 3438 57%; 2969 47%; 2672 63%; 2593 59%; 2362 72%; 1751 10%; 1595 79%; 1475 54%; 1438 53%; 1329 54%; 1301 59%; 1222 11%; 1171 3%; 1135 29%; 1090 21%; 1032 10%; 993 60%; 956 78%; 906 82%; 886 83%; 866 74%; 830 64%; 783 83%; 753 27%; 724 76%; 698 48%; 676 21%; 650 71%; 623 73%; 597 76%; 567 47%; 480 69%; 461 76%; 421 78%. XRPD [Cu Kalpha1]: Angle [2Theta]: Relative intensity [%] 6.79 32 8.27 33 8.59 59 12.44 21 12.62 22 13.07 31 13.55 62 16.87 59 17.24 63 18.25 14 19.00 71 19.69 52 20.02 19 20.24 47 21.34 100 21.82 17 22.40 42 22.72 19 23.02 50 23.27 25 23.65 47 24.75 49 25.09 33 25.34 56 25.85 18 27.11 25 27.61 19 28.12 22 32.14 15 32.55 20 32.97 14 35.10 11
With Ion exchange resin (Amberlite) (H+ form); In methanol;
Compound C-8 Ion exchange resin (Amberlite) (H+ form) was added to a solution of sodium 2-naphthalenesulfonate in methanol. The mixture was stirred overnight and filtered and the solvent was evaporated. The residue was lyophilized yielding 2-naphthalenesulfonic acid.
In methanol; at 0 - 55℃; for 20h;Heating / reflux;Product distribution / selectivity;
Clopidogrel hydrogensulfate, m.p. ~ 184 C (1.78 g) was dissolved inmethanol (25 ml) at a temperature of 55 C and naphthalene 2-sulphonic acid sodium salt (1.15 g) was added. The reaction mixture was vigorously stirred at reflux for 12 hours, and then cooled in a refrigerator for 8 hrs. The reaction mixture was filtered, evaporated to dryness and crystallised from isopropanol. From the cloudy solution the inorganic salt was filtered off and the filtrate was allowed to cool to 0 C. The solid was collected, washed with diethyl ether and dried at 35 C in a vacuum oven for 12 hours to obtain 1.9 g of clopidogrel napsylate.
99.2 g (58.9percent) of this compound and 82.8 g of 4-chloro-3-nitrobenzene-1-sulfonic acid (85.9percent) are suspended in 250 ml of water and the pH of the suspension is adjusted to 8 with dilute NaOH. After 15 hours at 112°-115° C. in a tantalium autoclave, the slurry is filtered and the filter cake is washed with sodium chloride solution and dried in vacuo at 60°-70° C. 129 g of the above nitro compound are added to 300 ml of water containing 60 g of iron powder and 3 ml of glacial acetic acid. The batch is refluxed for 20 minutes, then 4.8 g of sodium carbonate are added cautiously and iron residue is removed by filtration. The product is precipitated with sodium chloride and the precipitate is isolated by filtration, washed with sodium chloride solution and dried in vacuo at 60°-70° C. The yield of the chromatographically pure compound of the above formula is 126.4 g.
With pyridine; thionyl chloride; In chlorobenzene;
EXAMPLE 16 1 mol of sodium 2-naphthalenesulphonate and 7.0 g of pyridine are suspended in 600 ml of chlorobenzene and the suspension is warmed to 40 C. 143 g (1.2 mols) of thionyl chloride are added dropwise, whilst stirring, the mixture is warmed for a further 6 hours to 100 C. and the chlorobenzene and residual thionyl chloride are distilled off in vacuo. The yield of naphthalenesulphonyl chloride is 99%.
EXAMPLE 1 Sodium naphthalene-2-sulphonate 12.5 g. (0.054 moles) was dissolved in water (300 ml) at 35-40, filtered and cooled to 20. This was added with stirring to a solution of talampicillin HCL (25 g. activity weight, 0.048 moles) in water (500 ml) at 22-25 over 15 minutes. The solution was cooled to ca 5-10 and the product isolated by filtration, reslurried in water (250 ml) for 30 minutes and the product isolated and dried in a fluid bed dryer at 20-25 initially, then increasing the temperature gradually to 50. Yield 30 g. of talampicillin napsylate.
molecular sieve; In dichloromethane; water;
EXAMPLE 4 Sodium naphthalene-2-sulphonate (150 g.) was dissolved in water (4 liters) at 35-40, filtered, cooled to 20 and acidified with concentrated hydrochloric acid (60 ml.). This was added with stirring to a solution of talampicillin HCL (300 g. activity weight) in water (6.5 liters) at 22-25 over 15 minutes then cooled to 5-10. Precipitated product was isolated, reslurried in water (3.5 liters) re-isolated, dissolved in methylene dichloride (3.0 liters), separated from water and desiccated over molecular sieve (200 g. type 4A). The filtered solution was spray dried to give 320 g. of talampicillin napsylate.
With hydrogenchloride; In dichloromethane; water;
EXAMPLE 5 Sodium naphthalene-2-sulphonate (150 g.) and water (6.0 liters) were stirred for ca 15 minutes at 20-25. Hydrochloric acid (60 ml.), methylene dichloride (3.5 liters) and talampicillin HCL (300 g. activity weight) were then added, and stirring was continued for 15 minutes. The talampicillin napsylate produced was located entirely in the organic phase. After washing with water (4*5.0 liters) this was desiccated over molecular sieve prior to spray drying to give 350 g. of talampicillin napsylate.
In water;
EXAMPLE 6 A solution of sodium naphthalene-2-sulphonate was prepared by adding sodium naphthalene-2-sulphonate (12.5 g.) to a stirred solution of PVP (12.5 g.) in water (125 ml) at 35-40 C. After dissolution the solution was filtered, acidified with concentrated hydrochloric acid (5.0 ml.) and cooled to 20-25 C. Talampicillin hydrochloride (25 g.) was added to a stirred solution of PVP (25 g.) in water (250 ml.) at 20-25 C. When dissolved the solution was filtered into the precipitation vessel. The temperature was adjusted to 25-27 C. and the sodium naphthalene-2-sulphonate solution was added with stirring over ca 30 minutes. The slurry was cooled to 5-10 C. and filtered. The product was reslurried in water (250 ml.) and dried in a fluid bed drier to give 30 g. of talampicillin napsylate.[PVP m.wt:10,000].
N-(2-4'-benzyloxyphenoxypropyl)-3,4-dimethylphenylacetamidine naphthalene-2-sulphonate[ No CAS ]
[ 23194-54-9 ]
Yield
Reaction Conditions
Operation in experiment
In ethanol;
EXAMPLE 96 By the methods of the relevant parts of Example I, 4-benzyloxyphenol was converted to 2-4'-benzyloxyphenoxypropionitrile, b.p. 166-172/0.7 mm., m.p. 84-86 (95% ethanol) and thence to 2-4'-benzyloxyphenoxypropylamine, b.p. 158-160/0.12 mm. The reaction between the amine (2.6 g.), 3,4-dimethylphenyl(thioacetamide) (1.8 g.) and methyl p-toluenesulphonate (1.9 g.) was carried out by the method of the second paragraph of Example III. The reaction mixture was treated with an excess of an aqueous solution of sodium naphthalene-2-sulphonate. The crystalline product was recrystallized from a mixture of ethanol and water and from a mixture of ethanol and ether to give N-(2-4'-benzyloxyphenoxypropyl)-3,4-dimethylphenylacetamidine naphthalene-2-sulphonate, m.p. 82-86.
quinacridone/naphthalene sulfonic acid formaldehyde polymer[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 mi concentrated (95-98%) sulfuric acid. 31.2 G unsubstituted quinacridone (CROMOPHTALS RED 2020, Ciba Specialty Chemicals Inc.) is added at a temperature below 45C and the mixture is stirred for 10 minutes at 40-45C to dissolve the pigment. 39.7 G of a wet naphthalene SULFONIC acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% <strong>[532-02-5]2-naphthalene sulfonic acid sodium salt</strong> (Shanghai Shen Li Chemical Factory) is added at a temperature below 45C and the mixture is stirred for 15 minutes at 40 to 45C followed by the rapid addition of 3.2 G para formaldehyde. The reaction mixture is stirred for one hour at 58-60C, then poured into 2.5 I of ice water. The violet precipitate is stirred for 1 hour at 5-20 C, then filtered. The residue is washed with water to a pH of 2.5 and kept as presscake with a solid content of 13% by weight. Around 0. 5 G of the press cake are reslurried in 20 mi hot water yielding a bluish red colored liquid. It is filtered to remove little aggregated material. The filtrate is red and appears a dye solution. However, the electron micrograph shows the quinacridone in nanosize particle form with an average particle size of 4 to 25 nm.
poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); pigment blue 60; mixture of[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 ml concentrated (95-98%) sulfuric acid. 15 g C. I. Pigment Blue 60 (CIBANONE Blue RS PT 9860, Ciba Specialty Chemicals Inc.) are added at a temperature below 45oC and the mixture is stirred for 15 minutes at 40-45oC to completely dissolve the pigment. 10.7 g of a wet naphthalene sulfonic acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene sulfonic acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature below 50oC and the mixture is stirred for 10 minutes at 40-450C FOLLOWED by the rapid addition of 1.6 g para formaldehyde. The reaction mixture is stirred for one hour at 60-65oC then poured into 2.5 liter ice water. The dark bluish precipitate is stirred for 1 hour at 5-20oC, and then filtered. The dark bluish press cake is washed with water to a pH of 1.5-3. 0 and kept as presscake. About 0.5 g of the press cake are RESLURRIED in 20 ml hot water yielding a blue colored liquid which is filtered through paper to remove little aggregated material. The filtrate is blue and appears like a dye solution. However, the electron micrograph shows the indanthrone pigment in nanosize particle form with an average particle size of from 10 to 30 nm.
poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); 2,9-dichloroquinacridone; mixture of[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 250 mi concentrated (95-98%) sulfuric acid. 19.5 g 2, 9-dichloroquinacridone pigment (CINQUASIAO Magenta RT-265-D, Ciba Specialty Chemicals Inc.) are added at a temperature of 50oC and the mixture is stirred for 20 minutes at 48-52oC to dissolve the pigment. 19.9 g of a wet naphthalene sulfonic acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene sulfonic acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature BELOW 50oC and the mixture is stirred for 30 minutes at 45-50oC followed by the rapid addition of 1.6 G PARAFORMALDEHYDE. The reaction mixture is stirred for one hour at 58-60oC then poured into 2.5 liter ice water. The violet precipitate is stirred for 1 hour at 5-20oC, and then filtered. The violet press cake is washed with little water to a pH of 1.5-2. 5 and kept as presscake. About 0.5 g of the press cake are RESLURRIED in 20 ml hot water, yielding a violet colored liquid which is filtered through paper to remove little aggregated material. The filtrate is violet and appears like a dye solution. However, the electron micrograph shows the 2, 9-dichloroquinacridone in nanosize particle form with an average particle size of from 10 to 25 nm.
poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); 2,9-dimethylquinacridone; mixture of[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 ml concentrated (95-98%) sulfuric acid. 17 G 2, 9-DIMETHYLQUINACRIDONE pigment (CROMOPHTALS PINK PT, Ciba Specialty Chemicals Inc.) is added at a temperature below 45oC and the mixture is stirred for 10 minutes at 40-45oC to completely dissolve the pigment. 19.9 g of a wet naphthalene sulfonic acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene sulfonic acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature BELOW 45oC and the mixture is stirred for 30 minutes at 40-45oC followed by the rapid addition of 1.6 g para formaldehyde. The reaction mixture is stirred for one hour at 58-60oC then poured into 2.5 liter ice water. The bluish violet precipitate is stirred for 1 hour at 5-20oC, and then filtered. The violet press cake is washed with water to a pH of 2-2.5 and kept as presscake. About 0.5 g of the press cake are reslurried in 20 ML hot water yielding a magenta colored liquid which is filtered through paper to remove little aggregated material. The filtrate is magenta and appears like a dye solution. However, the electron micrograph shows the 2, 9-dimethyl quinacridone in nanosize particle form with an average particle size of from 10 to 30 nm.
poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); 2,9-dimethoxyquinacridone; mixture of[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 150 mi concentrated (95-98%) sulfuric acid. 14 g 2,9-dimethoxyquinacridone are added at a temperature below 45oC and the mixture is stirred for 10 minutes at 40-45oC to completely dissolve the pigment. 15 g of a wet naphthalene sulfonic acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene sulfonic acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature below 45oC and the mixture is stirred for 15 minutes at 40 to 45oC followed by the rapid addition of 1.2 g para formaldehyde. The reaction mixture is stirred for one hour at 58-60oC then poured into 2.5 liter ice water. The bluish violet precipitate is stirred for 1 hour at 5-20oC, then filtered. The bluish violet press cake is washed with water to a pH of 2-2.5 and kept as presscake. About 0.5 g of the press cake are reslurried in 20 ml hot water, yielding a bluish violet colored liquid which is filtered through paper to remove little aggregated material. The filtrate is bluish violet and appears like a dye solution. However, the electron micrograph shows the 2,9-dimethoxyquinacridone in nanosize particle form with an average particle size of from 10 to 30 nm.
poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); quinacridone; naphtalene sulfonic acid methyl metacridone; mixture of[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 ml concentrated (95-98%) sulfuric acid. 31.2 G unsubstituted quinacridone (CROMOPHTALO Red 2020, Ciba Specialty Chemicals Inc.) are added at a temperature BELOW 45C and the mixture is stirred for 10 minutes at 40-45C to dissolve the pigment. 39.7 G of a wet naphthalene sulfonic acid sodium SALT PRESSCAKE with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene SULFONIC acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature below 45C and the mixture is stirred for 15 minutes at 40-45C followed by the rapid addition of 3.2 G para formaldehyde. The reaction mixture is stirred for one hour at 58-60C then poured into 2. 5 1 ice water. The violet precipitate is stirred for 1 hours at 5-20C, then filtered. The violet press cake is washed with water to a pH of about 2.5 and kept as presscake. About 0.5 G of the press cake are RESLURRIED in 20 mi hot water yielding a red colored liquid which is filtered through paper to remove little aggregated material. The filtrate is red and appears like a dye solution. However, the electron micrograph shows the quinacridone in nanosize particle form with an average particle size of 4 to 25 nm. A small sample of the violet presscake is further washed to a pH of 5 and dried and analytically tested by MALDI. When measured in positive mode, it shows as main component quinacridone (m/z 314 peak), and only a trace of naphthalene SULFONIC acid methyl quinacridone (m/z 535 peak) is found as shown in Figure 1. When measured in negative mode, again the quinacridone is visible (m/z 312 peak) and the polymeric structure of the naphthalene sulfonic acid-formaldehyde polymer is clearly visible with the main molecular weight peaks at 428,649, 870,1091, 1312, 1534,1755 and 1976. The negative mode MALDI spectrum is shown in Figure 2.
poly(formaldehyde-co-1-naphtalene sulfonic acid sodium salt-co-2-naphtalene sulfonic acid sodium salt); pigment red 254; mixture of[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
A one-liter flask equipped with a stirrer, thermometer, condenser and drying tube is charged with 200 ml concentrated (95-98%) sulfuric acid. 21.4 g C. I. Pigment Red 254 (IRGAZINO DPP Red BO, CIBA Specialty Chemicals Inc.) is added and the mixture is stirred for 1 hour at 55-58oC. 23.9 G of a wet naphthalene sulfonic acid sodium salt presscake with a solid content of 58%, a mixture containing 80% 1-naphthalene sulfonic acid sodium salt and 20% 2- naphthalene sulfonic acid sodium salt (Shanghai Shen Li Chemical Factory) are added at a temperature below 70oC and the mixture is stirred for 10 minutes at 70oC followed by the rapid addition of 1.9 G para formaldehyde. The reaction mixture is stirred for one hour at 70-75oC, then poured into 2.7 liter ice water. The violet brownish precipitate is stirred for 1 hour at 5-20oC, then filtered. The press cake is washed with water to a pH of 2.0-3. 0 and kept as presscake. About 0.5 g of the press cake are reslurried in 20 ml hot water yielding a violet colored liquid which is filtered through paper to remove little aggregated material. The filtrate is brown and appears like a dye solution. However, the electron micrograph shows the diketopyrrolo pyrrole pigment in nanosize particle form with an average particle SIZE OF 10 TO 30 NM.
trans-1-[p-(N,N-dimethylamino)styryl]-3-methylimidazolium iodide[ No CAS ]
[ 532-02-5 ]
trans-1-[p-(N,N-dimethylamino)styryl]-3-methylimidazolium 2-naphthalenesulfonate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium hexaflorophosphate; In water;
General procedure: D2 (178 mg, 0.5 mmol) was dissolved in water (40 mL) andaddition of aqueous sodium salt of the corresponding anion(0.5 mmol) afforded precipitates which were filtered off, washedwith water and dried. Then the powders were obtained after driedunder vacuum. All salts were dried in a vacuum for 24 h to removesolvents before characterizing them byNMRand elemental analysis
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
