N-(2,3-Dihydro-2-oxo-1H-benzimidazol-5-yl)-3-hydroxy-2-naphthalenecarboxamide

In the diazo pot by adding 1000 kg water and 160kg30% hydrochloric acid, is added under agitation giving cash 150kg3-amino-4-methoxy compositions, beating 1 hours, with ice-cooling to 0 C the following, adjusting volume to 2500L, dissolved in advance of to 40% of the content of sodium nitrite (folding stem 42.5 kg sodium nitrite water 64 kg), measured end point keep the potassium iodide starch paper micro-blue, keeping temperature 5-10C, stirring 30 minutes, add 20 kg of diatomaceous earth, stirring 20 minutes, filtered salt solution.A small quantity of water of added to the coupling pot, open stirring, will giving cash 186.5kg5 - (2 the [...] -hydroxy -3 the [...] -naphthalene carboxamide yl) - 2-benzimidazolone adding the colloid rubs into randoms pot, by adding 0.6 kg eighteen alkane mellow base polyoxyethylene ether, beating 0.5 hours, adjusting volume to 1500L, adjusting temperature is 0-10C.The diazonium salt is slowly added to the pulping solution of 5 - (2 the [...] -hydroxy -3 the [...] -naphthalene carboxamide yl) - 2-benzimidazolone suspension coupling reaction in, at the same time, in the coupling process the mass concentration 20% of sodium bicarbonate solution dripped into randoms pan, maintain the reaction system pH value is 5.5-6.0, coupling component dropping time is 0.5-1 hours, randoms temperature 5-10C, randoms end, re-stirring and a half hours, heating to 70-80C, thermal insulation 1-2 hours, the invention aims to, rinse resulting pigment after the coarse filter.Added to the reaction kettle pyrrole winds the alkane alkone 2000L, adding the above-mentioned pigment crude, beating, raising the temperature to 100-110C, thermal insulation 2 hours, specifically pigment conversion situation, cooling to 40-50C, filtering, washing, 80 C drying, crushing C.I is obtained. Pigment red 176 finished product. Number is about 340 kg.27 parts of the compound (b-3) 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., Filtered, washed with water, and dried at 80 C. for 24 hours to obtain 45 parts of the pigment represented by the formula (5). 5 parts of the pigment of the formula (5) was crushed into 100 parts of 98% sulfuric acid and charged at 15 C. or less.Thereafter, the temperature was raised to 60 C., stirred for 2 hours, and slowly added dropwise to 2, 000 parts of cold acetone prepared separately. The precipitate was filtered, washed twice with 1000 parts of cold acetone, and dried at 80 C. for 24 hoursAnd dried for 6.1 parts of a red compound. As a result of mass spectrometric analysis by LC-MS, it was identified that the following compound (A-3) was the main component.The hydrochloric acid solution was in for the synthesis of the illustrated compound (2)was added to 19 g of compound (1) and completely dissolved by heating to an elevatedtemperature 70 C. Was dissolved in a solution of sodium nitrite was dropped after thecooled 40% aqueous solution of 40 g to 0 C and check what's not cheongbyeon withKI (Potassium iodide starch paper). Confirming the cheongbyeon solution was stirred for30 minutes at below 5 C. Stirred for 5 minutes by addition of acetic acid 80% aqueoussolution 8.2 g sodium acetate and 16.3 g thereof in the solution to obtain the compound(2). Compound (4) it was synthesized by using the intermediate compound (2). First, into a43.5 g of a compound of the different reactors (3) and the compound (2) was dissolvedin a 3% aqueous solution of caustic soda was added dropwise 450 ml. After injecting theresulting solution was dissolved by installing a dropping funnel to the reactor, themixture was slowly added dropwise. And determine the presence or absence of a redsolid precipitated in the reactor in the loading point, the reaction temperature wasmaintained at 10-15 C. After the reaction using a pH meter it was heated in a weaklyacidic atmosphere to 90 C. 90After reaching C by the addition of sodium chloridewere dissolved in 100 g. After sodium chloride was added to stop the heating and toobtain a rear, portion compound by washing, drying the water by filtration using aBuchner funnel (4) is stirred for 10 minutes.For the synthesis of the compound (2) shown above, 19 g of the compound (1) was added to an aqueous hydrochloric acid solution, and the mixture was heated to 70 C to dissolve completely.The dissolved solution was cooled to 0 , and 40 g of a 40% sodium nitrite aqueous solution was added dropwise, and KI paper (Potassium iodide starch paper) was used to confirm that cyanosis occurred. The solution in which the blue color was confirmed was stirred at 5 DEG C or lower for 30 minutes.To this solution was added 8.2 g of an 80% aqueous solution of acetic acid and 16.3 g of sodium acetate, and the mixture was stirred for 5 minutes to obtain a compound (2). First, 43.5 g of the compound (3) was added to a reactor different from the compound (2), and 450 ml of a caustic soda 3% aqueous solution was added dropwise to dissolve. A dropping funnel was installed in the reactor to inject the dissolved solution, and then slowly dropped.The presence or absence of red solid precipitation in the reactor is checked at the time of dropping, and the reaction temperature is10-15Respectively.After completion of the reaction, the mixture was heated to 90 DEG C in a slightly acidic atmosphere using a pH meter.When the temperature reached 90 DEG C, 100 g of sodium chloride was added and dissolved.After the addition of sodium chloride, heating was stopped and stirring was carried out for 10 minutes, followed by filtration using a Buchner funnel, washing with water and drying to obtain a compound (4).8.1 g of 5-amino-6-methylbenzimidazolone-(2) was stirred with 250 ml of water and 14.5 ml of 31.5% hydrochloric acid for 1 hour and then diazotized at 0 C. after the addition of ice, by adding an aqueous sodium nitrite solution. In a second vessel 16.0 g of 8.1 g of 5-amino-6-methylbenzimidazolone-(2) was diazotized with sodium nitrite solution in the same method as described in Example 1. 16.0 g of 5-(2'-hydroxy-3'-naphtoylamnio)-benzimidazol one-(2) was dissolved in 250 ml of water and 60 ml of 10% sodium hydroxide solution. This solution was added simultaneously with the diazo solution within 1 hour into a vigorously stirred buffer solution consisting of 350 ml of water, 20.4 g of sodium acetate, 7.0 ml of 20% acetic acid and 14 ml of 10% aqueous solution of the emulsifier described in Example 1. During the addition the pH was maintained at 5.2-5.5 and temperature was 55-60 C. The coupling was complete immediately after the addition of the components. The mixture was then heated for 1 hour at 95-98 C. The pigment was filtered and washed with hot water. The press cake was stirred with 450 ml of water and heated for 3 hours at 140 C. in a pressure vessel. After cooling, the pigment was filtered off, washed with hot water, dried at 80 C. and ground. 20.4 g of the violet pigment having similar properties as the pigment described before were obtained.4-Methylaminosulfonyl-p-cresidine (50.25 g) is dissolved in a solution of HCI (37.2 g) in water (516 ml). The solution is cooled to 0 C by addition of ice and to this is added a solution of NaNO2 (15.86 g) in water (75 ml). After 30 minutes stirring below 5C, activated charcoal (1.0 g) and amorphous silica (1.0 g) are added and the resulting mixture is filtered. The resulting clarified diazonium salt solution is kept below 5C and immediately prior to coupling excess nitrous acid is removed from the diazonium salt solution with sulphamic acid.In a separate vessel,

Molecular Weight:319.3
XLogP3:2.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:319.09569129
Monoisotopic Mass:319.09569129
Topological Polar Surface Area:90.5
Heavy Atom Count:24
Complexity:512
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes