CN101235213B - Light functional dye azo composite and preparation method thereof - Google Patents
Light functional dye azo composite and preparation method thereof Download PDFInfo
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- CN101235213B CN101235213B CN2007100371209A CN200710037120A CN101235213B CN 101235213 B CN101235213 B CN 101235213B CN 2007100371209 A CN2007100371209 A CN 2007100371209A CN 200710037120 A CN200710037120 A CN 200710037120A CN 101235213 B CN101235213 B CN 101235213B
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Abstract
The invention prepares a structure which couples substituted benzothiazole and substituted indole with azo bond. The compound with the structure has the advantages of simple synthesis and high stability, and overcomes the shortcoming existing in prior art of poor dye heat stability.
Description
Technical field
The invention belongs to the light functional dye technical field, be specifically related to azo class light functional dye that contains the benzothiazole group and preparation method thereof.
Background technology
CD storage technique is an information storage technology that grows up nineteen seventies, through the development of three more than ten years, has occurred jumbo high-density digital multifunctional optical disc now.
The technological core layer of DVD-R CD is that one deck is to the laser sensitive light functional dye of 635nm, because as the ablation process of the optical recording medium of DVD-R is that physics and the chemical transformation of recording medium under light and heat condition that the irradiation by laser beam causes realized writing of information, photo-thermal that should this optical recording medium is learned the important factor that characteristic is a decision material quality.This class azoic dyestuff of the present invention has outstanding advantage in this respect.
Summary of the invention
Existing compact disc dyestuff is not fine aspect solvability, the object of the present invention is to provide a kind of azo dyes compound, and it has synthetic simple, and solubility property is good, and the stability advantages of higher.
Another purpose of the present invention is to provide the preparation method of above-mentioned azo dyes compound, and follow-up coupled reaction can be carried out smoothly, reduces the generation of side reaction.
Azo dyes compound provided by the invention, its structure are as shown in the formula (as Fig. 1):
R wherein
1Be selected from hydrogen, C
1-6The straight or branched alkyl; R
2, R
3Be selected from hydrogen, C
1-6Straight or branched alkyl, R
4Be selected from hydrogen, C
1-6The straight or branched alkyl.
Aforesaid azo compound (Fig. 1) is characterized in that heat decomposition temperature is at 450-550 ℃.
Prepare the method for azo compound as mentioned above, wherein adopt following steps:
(1) Synthetic 2-N, N-R
2R
3N-R
4Indoles:
The indoles that adds 0.1mol part in the flask, the R that slowly adds 0.105-0.12mol part
2R
3R
4Electrophilic reagent, dropwise reflux 3-4h, reaction finishes and adds 200-300ml water and 100-200ml ethyl acetate extraction, organic phase is dry to be concentrated, and gets product (1);
(2) synthetic 3-nitro-2-N, N-R
2R
3N-R
4Indoles:
0.1mol part 2-N, N-R
2R
3-N-R
4Indoles is dissolved in 100-200ml part vitriol oil, be cooled to 0-5 ℃, slowly drip the mixed liquid of 0.10-0.12mol part concentrated nitric acid and 0.2-0.5mol part vitriol oil, dropwise, continue 0-5 ℃ and react half an hour down, reaction solution is poured in 300-500g part trash ice, be neutralized to pH=6 with strong aqua,, boil off solvent with 150-300ml part ethyl acetate extraction, with ethyl alcohol recrystallization, get product (2);
(3) synthetic 3-amino-2-N, N-R
2R
3-N-R
4Indoles:
0.1mol part 3-nitro-2-N, N-R
2R
3N-R
4Indoles is dissolved in 200ml part methyl alcohol, and stirring and dissolving adds 0.2-0.22g part palladium charcoal, feeds hydrogen, is heated to 50-60 ℃, stops reaction when hydrogen pressure no longer reduces, and removes the palladium charcoal, boils off solvent, gets product (3).
(4) synthetic 3-diazo-2-N, N-R
2R
3-N-R
4Indoles:
0.16-0.17mol part 3-amino-2-N, N-R
2R
3N-R
4Indoles is dissolved in 100ml part Glacial acetic acid, is cooled to 0-5 ℃, drips 22.1-23ml part vitriol oil, slowly adds 0.18-0.2mol part nitrosyl sulfuric acid then, dropwises and continues 0～5 ℃ of stirring 20 minutes, gets diazonium salt solution (4).
(5) 0.1mol part R
1-benzothiazole is dissolved in 200ml part methyl alcohol, and 0～5 ℃ drips down diazonium salt solution (3), dropwises to stir and spends the night, and adds 200ml part water, stirs half an hour, filter, evaporate to dryness, with the anhydrous methanol recrystallization, final product.
Prepare the method for above-mentioned azo compound, it is characterized in that adopting following steps:
(1) Synthetic 2-R
1Benzothiazole
0.1mol part 1-amino-2-mercapto phenyl formic-3-R
1Benzene is dissolved among 100ml part DMF, drips the 30ml DMF solution of 0.2mol part cyanamide under the nitrogen protection, dropwises to react 2-3h under the nitrogen protection under 100-120 ℃, stops reaction, is cooled to room temperature, and vacuum boils off the DMF solvent, gets product (1);
(2) Synthetic 2-R
1The benzothiazole diazonium salt
0.16-0.18mol part 2-R
1Benzothiazole is dissolved in 100ml part Glacial acetic acid, is cooled to 0～5 ℃, drips 22.1-23ml part vitriol oil, slowly adds 0.18-0.20mol part nitrosyl sulfuric acid then, dropwises and continues 0～5 ℃ of stirring 20 minutes, gets diazotization solution (2);
(3) 0.1mol part 2-N, N-R
2R
3N-R
4Indoles is dissolved in 200ml part methyl alcohol, and 0～5 ℃ drips down diazonium salt solution (2), dropwises to stir and spends the night, and adds 200ml part water, stirs half an hour, filter, crude product, evaporate to dryness, with the anhydrous methanol recrystallization, final product.
Aforesaid method is characterized in that used R
2R
3R
4Nucleophilic reagent comprise: dimethyl sulfoxide (DMSO), benzyl chlorine, C
1-4Halohydrocarbon etc.
Azo compound as mentioned above, its in light functional dye, the application in DVD-R video disc recording technical field.
The replacement benzothiazole that the present invention obtains and the coupling structure of indoles have synthetic simple, and the high advantage of stability, have overcome the low deficiency of original dyestuff solubility property.
Description of drawings
Fig. 1 is the general structure of azo compound of the present invention;
Fig. 2 is the synthetic route chart of embodiment 1;
Fig. 3 is the synthetic route chart of embodiment 2;
Fig. 4 is the synthetic route chart of embodiment 3.
Embodiment
Embodiment 1:(such as Fig. 2)
1.2-N, N-dimethyl-N-skatole synthetic:
0.1mol 2-amino-indoles (compound 2-1) is dissolved among the 50mL DMF, the 0.2mol dimethyl sulfoxide (DMSO) drips under room temperature.Dropwise and be heated to backflow, react 3 hours postcooling, add 200ml water, stirred 20 minutes, add the 100ml ethyl acetate, extraction separatory, organic phase anhydrous magnesium sulfate drying to room temperature.Boil off solvent and get product 16.5g, productive rate: 94.8%.
2.3-nitro-2-N, N-dimethyl-N-skatole synthetic:
0.1mol 2-N, N-dimethyl-N-skatole (compound 2-2) is dissolved in the 100ml vitriol oil, is cooled to 0-5 ℃, slowly drip the mixed liquid of the 0.11mol concentrated nitric acid and the 22ml vitriol oil, dropwise, continue 0-5 ℃ and react half an hour down, reaction solution is poured in the 300g trash ice, be neutralized to PH=6 with strong aqua, with the 150ml ethyl acetate extraction, boil off solvent, with ethyl alcohol recrystallization, get product 9.0g, productive rate: 41.1%.
3.3-amino-2-N, N-dimethyl-N-skatole synthetic:
0.1mol 3-nitro-2-N, N-dimethyl-N-skatole (compound 2-3) is dissolved in 200ml methyl alcohol, stirring and dissolving, and 0.2g palladium charcoal adds, hydrogen exchange, feed hydrogen, be heated to 50 to 60 ℃, when hydrogen pressure no longer reduces, stop reaction, remove the palladium charcoal, boil off solvent, get product 17.6, productive rate: 93.1%.
4.3-diazo-2-N, N-dimethyl-N-skatole synthetic:
0.16mol 3-amino-2-N, N-dimethyl-N-skatole (compound 2-4) is dissolved in the 100ml Glacial acetic acid, is cooled to 0-5 ℃, drip the 22.1ml vitriol oil, slow then 0.18mol nitrosyl sulfuric acid dropwises and continues 0～5 ℃ of stirring 20 minutes, get diazotization solution, stand-by.
5.0.1mol benzothiazole is dissolved in the 200ml methyl alcohol, 0～5 ℃ drips diazonium salt solution down, dropwises to stir and spends the night, and adds 200ml water, stir half an hour, filter, get crude product, evaporate to dryness, with the anhydrous methanol recrystallization, get final product: 22.4g, productive rate: 66.9%.
HNMR(400MHz)
2.85(s，6H)，3.60(s，3H)，6.5(m，2H)，6.8(d，1H)，7.0(d，1H)，7.55(d，2H)，8.12(d，1H)，8.23(d，1H)
Heat decomposition temperature: 460-475 ℃
Embodiment 2:(such as Fig. 3)
1.2-N, N-diethyl-N-skatole synthetic:
0.1mol 2-amino indole (compound 4-1) is dissolved among the 50mL DMF, the 0.4mol monobromethane adds, and is heated to backflow, react 3 hours postcooling to room temperature, add 200ml water, stirred 20 minutes, add the 100ml ethyl acetate, extraction separatory, organic phase anhydrous magnesium sulfate drying.Boil off solvent and get product 19.7g, productive rate: 91.3%.
2.3-nitro-2-N, N-diethyl-N-skatole synthetic:
0.1mol 2-N, N-2 ethyl-N-skatole (compound 4-2) is dissolved in the 100ml vitriol oil, is cooled to 0-5 ℃, slowly drip the mixed liquid of the 0.11mol concentrated nitric acid and the 22ml vitriol oil, dropwise, continue 0-5 ℃ and react half an hour down, reaction solution is poured in the 300g trash ice, be neutralized to PH=6 with strong aqua,, boil off solvent with the 150ml ethyl acetate extraction, get the dark oil thing, with sherwood oil: ethyl acetate=20: 1 is crossed column separating purification, product 9.7g, productive rate: 37.3%.
3.3-amino-2-N, N-diethyl-N-skatole synthetic:
0.1mol 3-nitro-2-N, N-dimethyl-N-skatole (compound 4-3) is dissolved in 200ml methyl alcohol, stirring and dissolving, and 0.2g palladium charcoal adds, hydrogen exchange, feed hydrogen, be heated to 50 to 60 ℃, when hydrogen pressure no longer reduces, stop reaction, remove the palladium charcoal, boil off solvent, get product 20.8, productive rate: 90.1%.
4.3-diazo-2-N, N-diethyl-N-skatole synthetic
0.16mol 3-amino-2-N, N-diethyl-N-skatole (compound 4-4) is dissolved in the 100ml Glacial acetic acid, is cooled to 0～5 ℃, drip the 22.1ml vitriol oil, slow then 0.18mol nitrosyl sulfuric acid dropwises and continues 0～5 ℃ of stirring 20 minutes, get diazotization solution, stand-by.
5.0.1mol benzothiazole is dissolved in the 200ml methyl alcohol, 0～5 ℃ drips diazonium salt solution (compound 4-5) down, dropwises to stir and spends the night, and adds 200ml water, stir half an hour, filter, get crude product, evaporate to dryness, with the dehydrated alcohol recrystallization, get final product: 22.4g, productive rate: 59.5%
HNMR：
1.13(m，6H)，1.51(m，3H)，3.09(d，2H)，3.39(d，4H)，6.5(d，2H)，6.8(s，1H)，7.0(d，1H)，7.55(d，2H)，8.12(d，1H)，8.23(d，1H)
Heat decomposition temperature: 476-490 ℃
Embodiment 3:(such as Fig. 4)
1.2-nitroindoline is synthetic
0.1mol indoles (compound 5-1) is dissolved in the 100ml vitriol oil, is cooled to 0～5 ℃, slowly drips the mixed liquid of the 0.11mol concentrated nitric acid and the 22ml vitriol oil, dropwise, continue 0～5 ℃ and react half an hour down, reaction solution is poured in the 300g trash ice, be neutralized to PH=6 with strong aqua, with the 150ml ethyl acetate extraction, boil off solvent, the dark oil thing, with sherwood oil: ethyl acetate=20: 1 is crossed column separating purification, get product 8.9g, productive rate: 54.9%.
2.2-nitro-N-isopropyl indole is synthetic
0.1mol 2-nitroindoline (compound 5-2) is dissolved among the 50ml DMF, is heated to 40 ℃, slowly drips the 30ml DMF solution of 0.12mol benzyl chlorine, adds the 0.2mol solid sodium carbonate after dropwising, and is heated to 80 ℃ then, reaction 12h in batches.Add 400ml water, the extraction of 200ml toluene, organic phase anhydrous magnesium sulfate drying.Boil off toluene, get the 21.6g product, productive rate: 85.7%.
3.2-amino-N-isopropyl indole is synthetic:
0.mol 2-nitro-N-isopropyl indole (compound 5-3) is dissolved in 200ml methyl alcohol, stirring and dissolving, and 0.2g palladium charcoal adds, hydrogen exchange, feed hydrogen, be heated to 50 to 60 ℃, when hydrogen pressure no longer reduces, stop reaction, remove the palladium charcoal, boil off solvent, get product 15.8g, productive rate: 91.1%.
4.2-N, N-dimethyl-N-isopropyl indole synthetic:
0.1mol 2-amino-N-isopropyl indole (compound 5-4) is dissolved among the 50ml DMF, the 0.2mol dimethyl sulfoxide (DMSO) drips under room temperature.Dropwise and be heated to backflow, react 3 hours postcooling, add 200ml water, stirred 20 minutes, add the 100ml ethyl acetate, extraction separatory, organic phase anhydrous magnesium sulfate drying to room temperature.Boil off solvent and get product 16.6g, productive rate: 82.2%.
5.3-nitro-2-N, N-dimethyl-N-isopropyl indole synthetic
0.1mol 2-N; N-dimethyl-N-isopropyl indole (compound 5-5) is dissolved among the 100ml DMF; nitrogen protection drips the 30ml DMF solution of 0.2mol cyanamide down; dropwise nitrogen protection and react 2h down for following 120 ℃; stop reaction, be cooled to room temperature, vacuum boils off the DMF solvent; get product 20.3g, productive rate: 74.1%.
6.3-amino-2-N, N-dimethyl-N-isopropyl indole synthetic
0.1mol 3-nitro-2-N, N-dimethyl-N-isopropyl indole (compound 5-6) is dissolved in 250ml methyl alcohol, stirring and dissolving, and 0.2g palladium charcoal adds, hydrogen exchange, feed hydrogen, be heated to 50 to 60 ℃, when hydrogen pressure no longer reduces, stop reaction, remove the palladium charcoal, boil off solvent, get product 18.8g, productive rate: 86.6%.
7.3-amino-2-N, N-dimethyl-N-isopropyl indole diazonium salt synthetic:
0.16mol 3-amino-2-N, N-dimethyl-N-isopropyl indole (compound 5-7) is dissolved in the 100ml Glacial acetic acid, is cooled to 0～5 ℃, drip the 22.1ml vitriol oil, slow then 0.18mol nitrosyl sulfuric acid dropwises and continues 0～5 ℃ of stirring 20 minutes, get diazotization solution, stand-by.
8.0.1mol 2-methylbenzothiazole (compound 5-9) is dissolved in the 200ml methyl alcohol, 0～5 ℃ drips diazonium salt solution (compound 5-8) down, dropwise to stir and spend the night, add 200ml water, stir half an hour, filter, get crude product, evaporate to dryness is with the anhydrous methanol recrystallization, get final product: 26.3g, productive rate: 69.8%.
HNMR：
1.56(d，6H)，2.35(s，3H)，2.85(s，6H)，4.04(m，1H)，6.5(d，2H)，6.8(d，1H)，7.0(d，1H)，7.35(d，1H)，7.43(d，1H)，7.93(d，1H)
Heat decomposition temperature: 483-502 ℃
Above-mentioned description to embodiment is can understand and apply the invention for ease of those skilled in the art.The person skilled in the art obviously can easily make various modifications to these embodiment, and needn't pass through performing creative labour being applied in the General Principle of this explanation among other embodiment.Therefore, the invention is not restricted to the embodiment here, those skilled in the art should be within protection scope of the present invention for improvement and modification that the present invention makes according to announcement of the present invention.
Claims (7)
1. light functional dye azo composite is characterized in that the structure of the indoles of the benzothiazole that replaces and replacement with the azo bond coupling, and general formula is expressed as follows:
R wherein
1Be selected from hydrogen, C
1-6The straight or branched alkyl; R
2, R
3Be selected from hydrogen, C
1-6Straight or branched alkyl, R
4Be selected from hydrogen, C
1-6The straight or branched alkyl.
2. azo compound as claimed in claim 1 is characterized in that heat decomposition temperature is at 450-550 ℃.
3. preparation is characterized in that adopting following steps as the method for the described azo compound of claim 1-2:
(1) Synthetic 2-N, N-R
2R
3N-R
4Indoles:
The indoles that adds 0.1mol part in the flask, the R that slowly adds 0.105-0.12mol part
2R
3R
4Electrophilic reagent, dropwise reflux 3-4h, reaction finishes and adds 200ml-300ml water and 100ml-200ml ethyl acetate extraction, organic phase is dry to be concentrated, and gets product (1);
(2) synthetic 3-nitro-2-N, N-R
2R
3N-R
4Indoles:
0.1mol part 2-N, N-R
2R
3-N-R
4Indoles is dissolved in 100-200ml part vitriol oil, be cooled to 0-5 ℃, slowly drip the mixed liquid of 0.10-0.12mol part concentrated nitric acid and 0.2-0.5mol part vitriol oil, dropwise, continue 0-5 ℃ and react half an hour down, reaction solution is poured in 300-500g part trash ice, be neutralized to pH=6 with strong aqua,, boil off solvent with 150-300ml part ethyl acetate extraction, with ethyl alcohol recrystallization, get product (2);
(3) synthetic 3-amino-2-N, N-R
2R
3-N-R
4Indoles:
0.1mol part 3-nitro-2-N, the N-R2R3N-R4 indoles is dissolved in 200ml part methyl alcohol, and stirring and dissolving adds 0.2-0.22g part palladium charcoal, feeds hydrogen, is heated to 50-60 ℃, stops reaction when hydrogen pressure no longer reduces, and removes the palladium charcoal, boils off solvent, gets product (3).
(4) synthetic 3-diazo-2-N, N-R
2R
3-N-R
4Indoles:
0.16-0.17mol part 3-amino-2-N, N-R
2R
3N-R
4Indoles is dissolved in 100ml part Glacial acetic acid, is cooled to 0-5 ℃, drips 22.1-23ml part vitriol oil, and slow then 0.18-0.2mol part nitrosyl sulfuric acid dropwises and continues 0～5 ℃ of stirring 20 minutes, gets diazonium salt solution (4).
(5) 0.1mol part R
1-benzothiazole is dissolved in 200ml part methyl alcohol, and 0～5 ℃ drips down diazonium salt solution (3), dropwises to stir and spends the night, and adds 200ml part water, stirs half an hour, filter, evaporate to dryness, with the anhydrous methanol recrystallization, final product.
4. preparation is characterized in that adopting following steps as the method for the described azo compound of claim 1-2:
(1) Synthetic 2-R
1Benzothiazole
0.1mol part 1-amino-2-mercapto phenyl formic-3-R
1Benzene is dissolved among 100ml part DMF, drips the 30ml DMF solution of 0.2mol part cyanamide under the nitrogen protection, dropwises to react 2-3h under the nitrogen protection under 100-120 ℃, stops reaction, is cooled to room temperature, and vacuum boils off the DMF solvent, gets product (1);
(2) Synthetic 2-R
1The benzothiazole diazonium salt
0.16-0.18mol part 2-R
1Benzothiazole is dissolved in 100ml part Glacial acetic acid, is cooled to 0～5 ℃, drips 22.1-23ml part vitriol oil, slowly adds 0.18-0.2mol part nitrosyl sulfuric acid then, dropwises and continues 0～5 ℃ of stirring 20 minutes, gets diazotization solution (2);
(3) 0.1mol part 2-N, N-R
2R
3N-R
4Indoles is dissolved in 200ml part methyl alcohol, and 0～5 ℃ drips down diazonium salt solution (2), dropwises to stir and spends the night, and adds 200ml part water, stirs half an hour, filter, evaporate to dryness, with the anhydrous methanol recrystallization, final product.
5. method as claimed in claim 3 is characterized in that used R
2R
3R
4Nucleophilic reagent comprise: dimethyl sulfoxide (DMSO), benzyl chlorine, C
1-4Halohydrocarbon.
6. as the described azo compound of claim 1-2, it is in the light functional dye Application for Field.
7. as the described azo compound of claim 1-2, its application in DVD-R video disc recording technical field.
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| CN103059598B (en) * | 2011-10-20 | 2014-04-02 | 上海拓引数码技术有限公司 | Azo blue-ray optical storage dye and preparation method thereof |
| CN107759477A (en) * | 2017-11-20 | 2018-03-06 | 阿里化学(常州)有限公司 | A kind of preparation method of p-nitrophenyl ethylamine hydrochloride |
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| CN1620691A (en) * | 2002-01-25 | 2005-05-25 | 西巴特殊化学品控股有限公司 | Optical recording materials having high storage density |
| CN1753955A (en) * | 2003-09-11 | 2006-03-29 | 三菱化学株式会社 | Azo-metal chelate dye and optical recording medium |
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| CN1620691A (en) * | 2002-01-25 | 2005-05-25 | 西巴特殊化学品控股有限公司 | Optical recording materials having high storage density |
| CN1753955A (en) * | 2003-09-11 | 2006-03-29 | 三菱化学株式会社 | Azo-metal chelate dye and optical recording medium |
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