Method of obtaining derivatives 3-aroilantra-(1,9-cd)isoxazole-6-one

FIELD: chemistry.

SUBSTANCE: invention relates to the method of obtaining the derivatives 3-aroilanra-(1,9-cd)isoxazole-6-one of the general formula where X - hydrogen, halogen or the lowest alkyl, which are used as intermediate products in synthesis of derivatives 7,8-phthalylclaridone used as dyes for various polymeric materials and polyester fibres. The essence of the method lies in boiling 1(triazene-N-sulfonate)-2-aroihtranquonine in spirit solution of alkali with the subsequent neutralisation by acetic acid.

EFFECT: simpler technology and safer process.

1 cl, 2 tbl, 3 ex

 

The invention relates to the chemistry and technology of intermediates and organic dyes and can be used at the enterprises of the aniline dye industry to obtain antrahinonovye dyes.

Known source materials for the production of 7,8-phthaloylation are 1-nitroanthraquinone-2-carboxylic acid and various aromatic amines. For example, 3-methyl-7,8-phthaloylation produced by interaction of 1-nitroanthraquinone-2-carboxylic acid with p-toluidine (Patent 262469, Germany, 1915, in Support., Bd 2. S.687).

The disadvantage of this method is the inaccessibility of the original products, the formation of by-products in the process of condensation, the low yield of the obtained dye.

The closest technological essence and the achieved result is a method of obtaining 3-rolante[1,9-cd]isoxazol-6-ones, based on heating the corresponding 1-azido-2-aroratrading in organic solvents (ermine L., levdansky, VA, Arnold E.V. // Chemistry of heterocyclic compounds, 1983, No. 1, s-25; Patent USSR 857128, 1981, bull. Fig. No. 31).

The disadvantage of obtaining 1 azido-2-aroratrading is the use of attestations acid or its alkali metal salts, which can form explosive mixtures with air (attestation acid), and prisutstvie and heavy metal (heavy metal azides are explosive), making it unsafe.

The problem solved by the invention is to create a new method of obtaining derivatives of 3-rolante[1,9-cd]isoxazol-6-it.

The technical result - the simplification of the process and expand the range of target products.

This technical result is achieved in the development of a new method of obtaining derivatives of 3-rolante[1,9-cd]isoxazol-6-it General formula I

where X is hydrogen, halogen or an alkyl group, which is that 1-(triazin-N-sulfonate)-2-aroratrading General formula II

boiled in alcoholic alkali solution, followed by neutralization with acetic acid.

The inventive product: derivatives of 3-rolante[1,9-cd]isoxazol-6-it formula I

where X has the above values.

Reagent: 1-(triazin-N-sulfonate)-2-aroratrading formula II

Reaction conditions: boiling alcoholic solution of alkali.

The proposed method allows to obtain derivatives of 3-rolante[1,9-cd]isoxazol-6-it is with high exit not previously used for this purpose 1-(triazin-N-sulfonate)-2-ariyatrakool.

The composition and structure of the obtained 3-rolante[1,9-cd]isoxazol-6-ones installed with what omashu elemental analysis and physical-chemical methods.

Example 1. 3-Rolante[1,9-cd]isoxazol-6-he

of 4.57 g (0.01 mol) 1-(triazin-N-sulfonate)-2-aroratrading is boiled in a flask under reflux with stirring in 50 ml of ethanol containing 0.4 g (0.01 mol) of sodium hydroxide, for 0.5-1 h, the Reaction mass is then cooled to 10-15°C, neutralized with acetic acid, diluted with 50-60 ml of water and the precipitated crystals filtered off, washed on the filter with 20-25 ml of water, dried at room temperature. The yield of product amounted to 2.83 g (87%). TPL=248-250°C. Found, %: N 4,53; 4,37. With21H11NO3. Calculated, %: N Or 4.31.

Example 2. 3-Rolante[1,9-cd]isoxazol-6-he

of 4.57 g (0.01 mol) 1-(triazin-N-sulfonate)-2-aroratrading is boiled in a flask under reflux with stirring in 40 ml of ethanol containing 0.4 g (0.01 mol) of potassium hydroxide in 40 minutes. The reaction mass is then cooled to 10-15°C, neutralized with acetic acid, diluted with 50-60 ml of water and the precipitated crystals filtered off, washed on the filter with 20-25 ml of water, dried at room temperature. The yield of product amounted to 2.86 g (88%). TPL=248-250°C. Found, %: N 4,20; to 4.41. C21H11NO3. Calculated, %: N Or 4.31.

The synthesis of the other 3-rolante[1,9-cd]isoxazol-6-ones performed similarly, their characteristics are shown in table 1.

Table 1

Features 3-rolante[1,9-cd]isoxazol-6-ones
№ p/pDeputy X*TPL. °Found N %FormulaCalculated N, %Output %
1N248-2504,53; 4,37C21H11NO3or 4.3187
2CH3261-2634,25; 4,07With22H13NO34,1384
3Cl300-3024,01; 3,80C21H10ClNO33,8989
4Br285-2873,37; 3,51C21H10BrNO3of 3.4685
* - shows the onset temperature of decomposition substances

The original synthesis of 1-(triazin-N-sulfonate)-2-aroratrading used to obtain 3-rolante[1,9-cd]isoxazol-6-ones, as follows.

Example 3. 1-(Triazin-N-sulfonate)-2-aroratrading

A solution of 3.27 g (0.01 mol) of 1-amino-2-aroratrading in 100 ml of acetic acid diasterous at 5-10°With solution nitrogylcerin acid prepared from 0,83 g (0,012 mol is) of sodium nitrite and 10 ml of 95% sulfuric acid, within 2 hours. Then the reaction mass is diluted with 10-15 ml of water, add activated charcoal and filtered from impurities. Then the filtrate with stirring and cooling gain of 1.43 g (0.012 mol) of sodium salt of sulfamic acid and 0,098 g (0.012 mol) of sodium acetate. Stand 15-20 minutes with stirring, then the reaction mixture is diluted with 100 to 150 ml of cold water, the precipitated crystals of 1-(triazin-N-sulfonate)-2-aroratrading filtered off, washed on the filter with cold water, dried at room temperature. The product yield was of 4.04 g (89%). TPL=121°C. Found, %: N 9,31, 9,12; S 6,88, 7,09. C21H12N3About6The SNa. Calculated, %: N 9,19; S 7,00.

The synthesis of the remaining 1-(triazin-N-sulfonate)-2-aroratrading is carried out in similar conditions. Characterization of the obtained compounds are shown in table 2.

Source 1-amino-2-aroratrading obtained in a known manner, when the acylation of aromatic hydrocarbons with acid chloride of 1-amino-2-anthracenemethanol acid in the presence of aluminium chloride (dokunikhin NS, Shane S.M., Boguslavskaya I.L. // Zhur.org.chem.. 1964. T. S).

The obtained derivatives of 3-rolante[1,9-cd]isoxazol-6-it can be used mainly in organic synthesis for the preparation of derivatives of 7,8-phthaloylation used as dyes for various polymer materials is impressive and polyester fibers.

Table 2

Features 1-(triazin-N-sulfonate)-2-aroratrading
№ p/pDeputy X*TPL°CFoundFormulaCalculatedOutput %
N%S%N %S %
1N1189,29; the remaining 9.086,79; 7,05C21H12N3About6SNa9,197,0089
2CH31268,81; 9,07to 6.58; 6,70With22H14N3About6SNa8,926,7987
3Cl1378,72; 8,636,37; 6,61C21H11ClN3About6SNa8,546,5190
4Br1307,98; 8,016,13; of 5.89C21H11BrN3O6SNato 7.845,9788
* - shows the onset temperature of decomposition substances/td>

The method of obtaining derivatives of 3-rolante[1,9-cd]isoxazol-6-it General formula

where X is hydrogen, halogen or lower alkyl,

the heat derived 2-aroratrading in an organic solvent, characterized in that as a derivative of 2-aroratrading using 1-(triazin-N-sulfonate)-2-aroratrading General formula

where X has the value

which is boiled in alcoholic alkali solution, followed by neutralization with acetic acid.



 

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FIELD: chemistry.

SUBSTANCE: invention relates to the method of obtaining the derivatives of 3-aroilantra(1,9-cd)isoxazol-6-one with the general formula of where X - hydrogen, halogen or the lowest alkyl, which are used as intermediate products in synthesis of derivatives 7,8-phthalylclaridone, used as dyes for the polyester fibres. The essence of the method lies in heating 1-hydroxytriazone-2-aroilantraquinone in acetic anhydride.

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< / BR>
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