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Structure of 137-52-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 137-52-0 |
Formula : | C18H14ClNO3 |
M.W : | 327.76 |
SMILES Code : | C1=C3C(=CC(=C1C(NC2=CC(=CC=C2OC)Cl)=O)O)C=CC=C3 |
MDL No. : | MFCD00051171 |
InChI Key : | WWXPGBMLOCYWLD-UHFFFAOYSA-N |
Pubchem ID : | 67305 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301+H311+H331-H315-H319-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338-P311 |
Class: | 6.1 |
UN#: | 3439 |
Packing Group: | Ⅲ |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 1 C.I. Pigment Red 269 a1) Preparation of an Anisbase Diazonium Salt Solution: 242 g of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong> are initially stirred homogeneously into an initial charge of 2532 g of water at room temperature, precipitated by addition of hydrochloric acid and cooled down to 10 C. with 1.5 kg of ice/water. The precipitated hydrochloride is diazotized with 138 ml of sodium nitrite solution (40%) to finally give a readily stirrable anisbase diazo solution. This solution has a clarifying aid added to it and is subsequently filtered off into a feed vessel. Excess nitrite is removed by addition of amidosulfonic acid. A2) Preparation of a Buffer for the Anisbase Diazonium Salt Solution: To an initial charge of 1884 g of ice/water are added 502 g of acetic acid and also 614 g of aqueous sodium hydroxide solution, and the temperature is held at room temperature after addition of 1 kg of water. A3) Preparation of a Solution of the Coupling Component (Naphthol): An initial charge of 2720 g of water containing a wetting aid is heated to 80 C. While stirring, 328 g of N-(5-chloro-2-methoxyphenyl)-3-hydroxynaphthalene-2-carboxamide are introduced and dissolved alkalinically. By addition of a further 2720 g of ice/water, the Naphthol AS solution is cooled down to room temperature. It is finally filtered by addition of a clarifying aid. a4) Azo Coupling in Microreactor: The anisbase diazonium salt solution and the Naphthol AS solution are pumped at a flow rate of 8 ml/min into the respective reactant inlets of the microreactor (type: Cytos from CPC-Systems/Frankfurt). To achieve the requisite pH of 4.8-5.0 for azo coupling, the reactant solutions are diluted with the acetic acid/acetate buffer prepared according to a2), shortly upstream of the reactor inlets. The buffer solution is likewise conveyed with the aid of calibrated piston pumps via a T-junction into the reactant feed lines of the microreactor at a flow rate of 6 ml/min in each case. The heat exchanger circuit of the microreactor is connected to a thermostat which sets the desired reaction temperature of 20 C. to 35 C. The coupled pigment suspension (21 C., pH=5.0) is collected in a feed vessel and subjected to the following solvent wash. b) Solvent Wash: The pigment suspension obtained from the microreactor is admixed with such an amount of butoxyethanol that the entire slurry contains about 10% by volume of butoxyethanol. The slurry is stirred at about 45 C. for 30 minutes, filtered off and washed with water. After sampling, the colorant-solvent-water suspension is subjected to the following membrane purification. c) Membrane Purification: A ceramic multichannel microfiltration membrane having a nominal separation limit of 60 nm for the separation-selective layer and a membrane area of 0.09 m2 is used. About 15 kg of the colorant suspension having a pigment content of about 2% by weight are charged to a temperature-controllable feed vessel. The membrane is subjected to a pressure of about 1.5 bar on the retentate side at ambient temperature. To ensure a constant volume in the feed vessel, the mass of permeate removed is replaced with demineralized water in a discontinuous manner. The pigment is fully retained and the organic secondary components are reduced to the values listed in table 2, under these conditions. The exchange volume (i.e., volume of demineralized water supplied/volume of pigment suspension used) is about 4. Permeate flux is about 200 l/(m2·h·bar). At the same time, the initial chloride ion content of 2.5% is reduced by 10 hours of diafiltration to 920 ppm as is the sulfate content from initially 0.3% to 30 ppm. d) Analysis: The samples taken (each 0.5 g) are dried, admixed with 10 ml each of N-methylpyrrolidone and comminuted for 15 min by ultrasonication. After addition of 20 ml of methanol and renewed grinding for 15 min, the suspension is filtered off. In each case, 20 mul of the filtrate are introduced into the autosampler of the HPLC system and detected by UV-V is detector at 240 and 375 nm (separating column Nucleosil 120-5 C18 (length: 25 cm, Øi=4.6 mm); mobile phase consisting of a buffer (575 mg of NH4H2PO4 plus 1000 g of H2O plus 3.0 g of NaN3 (pH 5.0)) and methanol chromasolv in various compositions for a total flux of 1 ml/min). | ||
50 parts of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong> (trade name: M-40, manufactured by Samsung Chemical Industry Co., Ltd.) was added to 1000 parts of water to disperse it, and the liquid temperature was adjusted to 0 to 5 C 35% hydrochloric acid 78 parts After stirring for 20 minutes, 15 parts of sodium nitrite was added by a method of diazotization by a predetermined method. 25 parts of 80% acetic acid and 15 parts of sodium acetate were added to prepare the diazonium salt, and 1 part of the triazine compound obtained in Production Example 1 was added to prepare a diazonium salt solution.69 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthalenecarboxamide (trade name: NAPHTHOL AC-CA, manufactured by Samsung Chemical Industries, Ltd.) And 48 parts by weight of a 30 wt% sodium hydroxide aqueous solution were mixed to prepare a coupling solution.The coupling liquid was adjusted so that the liquid temperature was 10 C or less, and the mixture was heated to 90 C for 30 minutes while stirring in the above-mentioned diazonium salt solution to produce an azo red pigment C.I. Pigment Red 269.The reaction solution was allowed to stand at room temperature, filtered, washed with water and dried in a predetermined manner, and then pulverized by a small pulverizer to obtain a reaction mixture containing a triazine compound represented by the formula (10) and an azo red pigment CI pigment Red 269 of the fine pigment composition 121 parts.Example 1See also1Google Translate for Business:Translator ToolkitWebsite Translator | ||
24.2 parts of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong> as a base component was added to 294 parts of water,Stirring to prepare a suspension,Further, 137 parts of ice was added to adjust the temperature to 5 C. or lower.To this was added 31.6 parts of 35% hydrochloric acid,And the mixture was stirred for 30 minutes. after that,An aqueous solution prepared by adding 7.1 parts of sodium nitrite to 14 parts of water was added and stirred for 1 hour to perform diazotization.2 parts of sulfamic acid was added to the reaction mixture,Nitrous acid was eliminated. To this was added a buffer solution consisting of a mixture of 36.5 parts of 25% sodium hydroxide aqueous solution, 36.5 parts of ice and 37.7 parts of 80% -acetic acid to prepare a solution containing a diazo component.On the other hand, 33.4 parts of N- (5-chloro-2-methoxyphenyl) -3-hydroxy-2-naphthamide as a coupler component was added to a mixed solution of 66.8 parts of water and 66.8 parts of dimethylsulfoxide, Followed by stirring and suspension. Then, 32.6 parts of 25% sodium hydroxide aqueous solution was added thereto, the mixture was further stirred for 30 minutes, and 66.8 parts of water was added to prepare a coupler solution. This dissolutionThe solution was added to the solution containing the diazo component over 20 minutes to carry out the coupling reaction.After stirring for 1 hour, the slurry was heated to 30 C. and further stirred for 30 minutes. This slurry was further heated to 50 C. and stirred for 30 minutes, followed by filtration and washing with water to obtain a pigment press cake. This press cake was dried at 90 C. for 18 hours and then pulverized to obtain 55.5 parts of pigment A. Example 1 is a reference example. |
27 parts of the compound (b-1) and 96 parts of a 25% sodium hydroxide aqueous solution were dissolved in 208 parts of methanol to prepare a coupler solution. On the other hand, 20 parts of the compound (a-1) was dispersed in 320 parts of water, ice was added to adjust the temperature to 5 C., 36.3 parts of a 35% hydrochloric acid aqueous solution was added and stirred for 1 hour and then sodium nitrite Was added to 19.2 parts of water to prepare an aqueous solution, and the mixture was stirred for 2 hours. An aqueous solution comprising 93 parts of 80% acetic acid aqueous solution, 106 parts of 25% sodium hydroxide aqueous solution and 112 parts of water was added to prepare an aqueous diazonium salt solution.The coupler solution was injected into the aqueous solution of diazonium salt at 5 C. over 30 minutes to carry out a coupling reaction. After stirring for 2 hours, after disappearance of the diazonium salt was confirmed, it was heated to 60 C., Filtration, washing with water, and drying at 80 C. for 24 hours to obtain 46 parts of the pigment represented by the formula (3). 5 parts of the pigment of the formula (3) was pulverized into 100 parts of 98% sulfuric acid and charged at 15 C. or less. That, The temperature was raised to 50 C., stirred for 2 hours, and slowly added dropwise into 2000 parts of cold acetone prepared separately. The precipitate was filtered, washed twice with 1000 parts of cold acetone, and heated at 80 C. for 24 hoursAnd dried to obtain 6.1 parts of a red compound. As a result of mass spectrometry by LC-MS, it was identified that the following compound (A-1) was the main component. |
Tags: 137-52-0 synthesis path| 137-52-0 SDS| 137-52-0 COA| 137-52-0 purity| 137-52-0 application| 137-52-0 NMR| 137-52-0 COA| 137-52-0 structure
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