6(7)-halogen-1,3 .3m-trichlorotoluene as intermediate products for the synthesis of dehalogenation phthalocyanines or their complexes

 

(57) Abstract:

The present invention relates to new derivatives of 1-amino-3-iminoisoindolin, which can be used as intermediate products in the synthesis of new dehalogenation phthalocyanines and their complexes used as dyes, catalysts, organic semiconductor materials, etc.

The task of the technical solution is the development of new compounds, intermediates for the synthesis of new dehalogenation phthalocyanines.

The problem is solved by the synthesis 6/7-halogen-1,3 .3m-trichloroaniline.

6/7-chloro - 6/7-bromo-1,3 .3m-trichlorotoluene obtained by interaction of the corresponding 4-chloro - or 4-bromophthalimide, respectively with phosphorus pentachloride when heated in dry 1,2-dichlorobenzene with subsequent fractional vacuum distillation. 2 Il.

The present invention relates to new derivatives of 1-amino-3-iminoisoindolin formula I, which can be used as intermediate products in the synthesis of new dihalogen-substituted phthalocyanines and their complexes used as dyes, organic semiconductor materials, etc. isoindoline II, used for the synthesis of dinitrotoluene phthalocyanines and their complexes [Young J. G. Onyebuagu W. J. Org. Chem. 1990, vol. 55, No. 7, p. 2155 2159] However, in this case are only dinitrotoluene phthalocyanines.

Dehalogenation phthalocyanines can be obtained by three prominent ways.

1. Direct halogenoalkane [Venkataraman K. the Chemistry of synthetic dyes, so-5, L. Chemistry 1977, 432 p]

In this case, we have a mixture of products containing phthalocyanines with different degree of halogenation, divide which currently is very difficult.

2. The condensation reaction using equimolar quantities gelegentlich and phthalic acids or their derivatives [Kiriyma G. Fukada N. The Science Report of the Niigata University. Ser.C. 1971, N 3, p. 9 21]

However, in this case also produces a mixture of products with different content of halogen.

3. Getting dehalogenation phthalocyanines through aminosilane, which, in turn, synthesize recovery dinitrotoluene phthalocyanines [Venkataraman K. the Chemistry of synthetic dyes, so 5. L. Chemistry, 1977, 432 p] These operations are tedious, time-consuming, and the products after each operation requires thorough cleaning.

Such social connections with a fixed position of the substituents, products require long and laborious operations for separation and purification.

The task of the technical solution is the development of new compounds that may find use as intermediates in the synthesis of new dehalogenation phthalocyanines.

The problem is solved by the synthesis 6/7-halogen-1,3 .3m-trichlorethane.

6/7-halogen-1,3 .3m-trichlorotoluene are solid light yellow products. Dissolved in tetrahydrofuran, acetone. Melt temperatures: 35oC 6/7-chloro-1,3 .3m-trichlorethane, 75oC - 6/7-bromo-1,3 .3m-trichlorethane. In the IR spectra of the claimed compounds (Fig. 1, 2) it is possible to allocate a number of common absorption bands. Thus, in the region 3100 3500 cm-1, 1580, 1620 cm-1there are bands that are characteristic of isoindoline fragments. The bands at 800 to 900 cm-1belong to the stretching vibrations of the C-Cl. In addition, 6/7-bromo-1,3 .3m-trichlorotoluene in the IR spectrum is observed absorption band at 510 cm-1typical for connection C-Br [Dyer D. R. Application of absorption spectroscopy of organic compounds. M. Chemistry, 1970, S. 31 68]

The claimed compound obtained by the interaction of the corresponding 4-chloro or 4-Pompey distillation [I. G. Young Onuebuagu W. I. Org. Chem. 1990, vol. 55, No. 7, p. 2155 2159]

Example 1. Getting 6/7-chloro-1,3 .3m-trichlorotoluene. In a 250 ml flask equipped with a stirrer with trap, reflux condenser and potassium chloride tube, place of 19.2 g (0,106 mol) 4-harptallica, to 46.7 g (0,224 mol) petaluridae phosphorus and stirred in 80 ml of dry 1,2-dichlorobenzene. The reaction mass is heated to 105oC and kept at this temperature and constant stirring for 170 hours, the Reaction mixture was cooled to room temperature and remove volatile compounds at low vacuum, then slowly heated and vacuum distillation at 110oC remove phosphorus oxychloride and the solvent is 1,2-dichlorobenzene. Then, when 153oC/ 7 Torr distilled target product. The compound obtained is dissolved in tetrahydrofuran, acetone. Melts at a temperature of 35oC. Yield: 10.0 g (37%).

WITH8H3HCl4< / BR>
M=254,9

Calculated C-37,7; H-1,2; N-5,5; Cl-55,7.

Found, C 38,0; H 1,4; N 5,4; Cl 55,7.

Example 2. Synthesis of 6 and 7-bromo-1,3 .3m-trichlorotoluene.

In a 250-ml round-bottom flask equipped with a stirrer with trap, reflux with potassium chloride tube, placed 31.0 g (0,137 mol) of 4-bromophthalimide heated to 105oC and maintained at this temperature and constant stirring for 170 hours, the Reaction mixture was cooled to room temperature and remove volatile compounds at low vacuum, then slowly heated and vacuum distillation at 110oC remove phosphorus oxychloride and the solvent is 1,2-dichlorobenzene. The target product is distilled at 170o/10 Torr. The compound obtained is dissolved in tetrahydrofuran and acetone. Melts at a temperature of 75oC. Output: 6,1 g (20%).

C8H3HCl3Br

M=299,4

Calculated C -32,1; H 1,0; N 4,7; 35,5 Cl; Br 27,0.

Found, C And 32.3; H 0,9; N 4,5; Cl 35,4; Br 27,0.

Example 3. Synthesis of 4,4"-Dichlorotoluene

In a round bottom flask with a capacity of 100 ml, equipped with a magnetic stirrer, is placed 0,100 g (of 0.68 mmol) 1-amino-3-iminoisoindolin and 0.2 ml (0,136 mmol) of triethylamine. With constant stirring in a stream of dry argon add 60 ml of dry tetrahydrofuran. After almost complete dissolution of 1-amino-3-iminoisoindolin the mixture is cooled to 0oC and added dropwise within 30 min 20 ml of tetrahydrofuran containing 0,173 (of 0.68 mmol) 6/7-chloro-1,3 .3m-trichlorotoluene. Maintain the mixture at 0oC for 1 h, and then slowly raise the temperature of the reed), the solution is returned to the reaction vessel, equipped with stirrer and reflux condenser. Add 0,074 g (of 0.68 mmol) of hydroquinone and to 0.108 g (2 mmol) of sodium methylate. The mixture is boiled in a stream of argon for 6 hours. The reaction mixture is cooled, filtered. The precipitate is washed with water, acetone, ethanol and dried. 4,4"-dichlorofluorene dark blue powder, practically insoluble in organic solvents, soluble in concentrated sulfuric acid. Output: 0,021 g (10,6%). The individuality of the compounds is confirmed by the data of elemental analysis, electronic, and vibrational spectroscopy.

C32N8H16Cl2< / BR>
M 583,5

Calculated C -65,9; H 2,8; N 19,2; Cl 12,2.

Found, C 66,0; H 3,0; N 18,9; Cl 11,5.

ESP (sulfuric acid),maxnm: 842; 790.

Example 4. Synthesis of 4,4"-Dichlorotoluene copper.

In a round bottom flask with a capacity of 100 ml, equipped with a magnetic stirrer, is placed 0,100 g (of 0.68 mmol) 1-amino-3-iminoisoindolin and 0.2 ml (0,136 mmol) of triethylamine. With constant stirring in a stream of dry argon add 60 ml of dry tetrahydrofuran. After almost complete dissolution of 1-amino-3-iminoisoindolin the mixture is cooled to 0oC and add the t mixture at 0oC for 1 h, and then slowly raised to room temperature and stirred for 6 hours is Filtered off the precipitate (triethylamine hydrochloride), the solution is returned to the reaction vessel, equipped with stirrer and reflux condenser. Add 0,076 g (0,56 mmol) of anhydrous copper chloride (1) and stirred in a stream of argon for 13 h, then the reaction mixture contribute 0,092 g (1.7 mmol) of sodium methylate and 0.124 g (1.13 mmol) of hydroquinone and boil this mixture for another 6 hours the Reaction mass is then cooled, filtered. The precipitate is washed with water, acetone, ethanol and dried.

4,4"-dichlorofluorene copper dark blue powder, practically insoluble in organic solvents, soluble in concentrated sulfuric acid. Output: of 0.081 g (36,9%). The individuality of the complex is confirmed by the data of elemental analysis, electronic, and vibrational spectroscopy.

C32N8H14Cl2Cu

M 645,0

Calculated C to 59.6; H 2,2; N 17,4; Cl 11,0; Cu 9,9

Found, C, 60,3; H 2,4; N 17,2; Cl 10,5; Cu 10,0

ESP (sulfuric acid),maxnm: 797; 704.

Example 5. Synthesis of 4,4"-dibromofluorene.

Synthesis behave analogously to example 3. Instead 6/7-chloro-1,3 .3m-trichlorethylene use 0,203 g (0,6 what I in organic solvents, dissolves in concentrated sulphuric acid.

Yield: 0.025 g (10,9%).

The identity of the compounds is confirmed by the data of elemental analysis, electronic, and vibrational spectroscopy.

C32N8H16Br2< / BR>
M 672,4

Calculated C 57,2; H 2,4; N 16,7; Br 23,8

Found, C 56,8; H 2,2; N 16,9; Br 24,0.

ESP (sulfuric acid), maxnm: 836, 784.

Example 6. Synthesis of 4,4"-dibromofluorene copper

Synthesis behave analogously to example 4. Instead 6/7-chloro-1,3 .3m-trichlorotoluene use 0,203 g (of 0.68 mmol) 6/7-bromo-1,3 .3m-trichlorotoluene.

4,4"-dibromofluorene copper dark blue powder, practically insoluble in organic solvents, soluble in concentrated sulfuric acid. Output: 0,051 g (20,4%).

The identity of the compounds was confirmed by the data of elemental analysis, electronic, and vibrational spectroscopy.

C32N8H14Br2Cu

M 733,9

Calculated C to 52.4; H 1,9; N 15,3; Br 21,8; Cu 8,7

Found, C 51,9; H 2,1; N 15,1; Br 22,0; Cu 8,5

ESP (sulfuric acid),max,, nm: 799, 704.

Thus, the claimed 6/7-chloro - 6/7-bromo-1,3 .3m-trichlorotoluene are organic substances class production is x complexes, identity structure and the presence of Halogens with a fixed position in the molecule of the phthalocyanine.These properties allow the use of metalphthalocyanine as organic semiconductors, catalysts, dyes, as well as in other branches of science and technology. In addition, dehalogenation metalphthalocyanine can be used for synthesis of other disubstituted metallophthalocyanines.

6(7)-Halogen-1,3 .3m-trichlorotoluene formula

< / BR>
where Hal is Cl, Br,

as intermediate products for the synthesis of dehalogenation phthalocyanines or their complexes.

 

Same patents:

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15 cl, 2 tbl, 27 ex

Compounds // 2327690

FIELD: chemistry.

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12 cl, 9 tbl, 265 ex

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17 cl, 188 ex

FIELD: chemistry.

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8 cl, 11 ex

FIELD: chemistry.

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27 cl, 4 tbl, 72 ex

FIELD: chemistry.

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20 cl, 2 tbl, 12 dwg, 382 ex

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3 dwg, 2 tbl, 3 ex

FIELD: medicine, pharmaceutics.

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EFFECT: obtaining pharmaceutical composition, which has agonistic activity with respect to EDG-1, EDG-6 and/or EDG-8, containing as active component invention compound, to method of prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8 invention compounds, to method of prevention and/or treatment of disseminated sclerosis and method of immune reaction suppression and/or induction of lymphopenia, to application of invention compounds for obtaining medication for prevention and/or treatment of disease, conditioned by EDG-1, EDG-6 and/or EDG-8, to application of compounds for obtaining medication for prevention and/or treatment of disseminated sclerosis, to application of compounds for obtaining immunodepresant and/or medication inducing lymphopenia and to crystal forms of some individual compounds.

17 cl, 10 dwg, 5 tbl, 251 ex

FIELD: medicine, pharmaceutics.

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EFFECT: compounds possess BACE inhibitory activity.

8 cl, 6 tbl, 136 ex

FIELD: chemistry.

SUBSTANCE: copolycarbonate contains an isomeric mixture of the following formulae as a repeating monomer unit:

,

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, where R3 and R4 denote hydrogen, an alkyl with 1-18 carbon atoms, an alkoxy with 1-18 carbon atoms, a halogen, respectively, if needed, a substitued aryl or arylalkyl, and X is a single bond, -SO2-, -CO-, -O-, -S-, an alkylene with 1-6 carbon atoms, an alkyidene with 2-5 carbon atoms or a cycloalkylidene with 5-6 carbon atoms, which can be substituted with an alkyl with 1-6 carbon atoms, an arylene with 6-12 carbon atoms, which, if needed, is condensed with aromatic ring groups containing heteroatoms.

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9 cl, 9 ex

Phthalocyanines // 2278120

FIELD: organic chemistry, metalloorganic compounds.

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EFFECT: valuable properties of compounds.

3 cl, 1 tbl, 2 ex

FIELD: printing inks.

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EFFECT: enabled effective protection of articles or substrates when using printing inks containing, for example, blue or green dyes, whose absorption bands can be shifted to infrared region and partially mask absorption properties of marker.

20 cl, 4 tbl, 6 ex

FIELD: chemistry of metalloorganic compounds, chemical technology.

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EFFECT: improved and valuable properties of substance.

3 dwg, 2 ex

FIELD: chemistry of metalloorganic compounds, chemical industry.

SUBSTANCE: invention relates to a novel compound, namely, to copper tetra-4-({4'-[(4''-octyloxybenzoyl)oxy]benzoyl}oxy)phthalocyanine of the formula: Proposed compound provides preparing the more saturated and uniform coloring on paraffin and polystyrene as compared with it's the nearest analogue with respect to structure and using. Proposed compound can be used as a lipid-soluble dye for staining hydrocarbons, waxes, polymeric materials and rubber.

EFFECT: improved and valuable properties of compound.

4 dwg, 2 ex

FIELD: chemistry.

SUBSTANCE: invention refers to chemical industry, i.e. to the new chemical compounds 4-(1-benzotriazole)-5-(naphtaoxy)-phtalodinitriles of the general formula in which R stands for as the basic for synthesis of copper tetra-4-(1-benzotriazole) tetra-5(2-naphtaoxy)phthalocyanine and copper tetra-4-(1-benzotriazole) tetra-5(1-naphtaoxy)phthalocyanine which are the solvent dyes for waxes, synthetic fiber, polymers, hydrocarbons, fats, alcohols, plastic materials and resin elastic colouring.

EFFECT: end dyes are dissolved effectively in organic environments.

1 cl, 4 dwg, 5 ex

FIELD: chemistry.

SUBSTANCE: invention refers to new chemical compound of copper tetra-4-(4- morpholine-4-yl)-tetra-5-(phenoxy)phthalocyanine being a soluble dye to be used for dyeing hydrocarbons, waxes, oils, alcohols, polymer materials, plastics, rubber, and synthetic fibres.

EFFECT: improved compounds.

1 cl, 2 ex, 2 dwg

FIELD: chemistry.

SUBSTANCE: invention concerns novel compound of zinc mezzo-triphenyltetra-[-(п-triphenylmethylphenoxybenzo)]monoazaporphyrinate.

EFFECT: possible application as fat-soluble green colourant for polymers, as material for thin film microelectronics, as catalyst, and in other scientific and technical fields.

1 cl, 1 ex, 1 dwg

FIELD: printing.

SUBSTANCE: invention relates to a set of inks to create images using an inkjet printer including a set of inks with six kinds of inks for inkjet printer. Set of inks contains black inks, including the first system of organic solvents, blue inks, including a second system of organic solvents, purple inks, including a third system of organic solvents, and yellow inks comprising a fourth organic solvent system. In this case at least two systems of organic solvents are different. The first system of organic solvents includes the first organic solvent and a second organic solvent. The second and third systems of organic solvents include the first organic solvent and the third organic solvent. The fourth organic solvent system includes a second organic solvent and a fourth organic solvent.

EFFECT: offered set of colouring agents is characterised by compatibility of colouring agents and provides printing images with the jet printer of wide colour gamma, resistant to discoloring.

7 cl, 6 tbl, 1 ex

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