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With N,N-dimethyl acetamide; Phthaloyl dichloride; In 1,4-dioxane; at 70℃; for 3h;
N, followed by stirring N- dimethylacetamide 4.3 g (49 mmol) and phthalic acid chloride 10.4 (51.5 mmol) at 30 C.. Reaction solution became impossible stirring immediately change to brown solidified. Overall the addition of 1,4-dioxane 50mL became homogeneous. It became a homogeneous solution and stirred 70 C.. 3 hours in suspension in addition 2,6-naphthalene dicarboxylic acid 4.3g (20 mmol). The solid was collected by filtration precipitated by cooling to room temperature, and dried after washing with 1,4-dioxane and hexane 2,6-naphthalene dicarboxylic acid chloride 4.5g was obtained. The yield was 89%.
85%
With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; water; at 75℃; for 12h;Cooling with ice; Inert atmosphere;
A solution of 10.810 g (0.050 mmol) of 2,6-naphthalene dicarboxylic acid was added to a 250 ml three-necked flask, was added 100ml of water in addition to dichloromethane and 17.846 g (0.150 mol) of thionyl chloride was slowly added dropwise under ice-cooling, 3 to 4 drops of N, N-dimethylformamide was added dropwise as a catalyst, magnetically stirring with argon gas heated to 75 C the reaction was refluxed for 12h. The solvent was evaporated under reduced pressure and excess sodium dichlorosulfoxide to give a pale yellow solid in 85% yield. The intermediate structure is as follows:
84%
With Vilsmeier reagent; In 1,4-dioxane; at 60℃; for 1h;
A mixture of naphthalene-2,6-dicarboxylic acid 0.93 g (4.3 mmol) and VR7 1.11 g (8.7 mmol) in 1,4-dioxane (5 mL) was stirred at 60 C for 1 h. The appearance in the flask changed from slurry to clear solution, and it was cooled to room temperature and filtered to give napthalene-2,6-dicarbonyl dichloride 0.91 g (84% yield) having mp 188-190 C (lit. 17 mp 189-190 C). GC-MS: m/z = 253(M+). IR (KBr): 1751 cm-1.
With thionyl chloride;
2) Synthesis of 2,6-Naphthalenedicarboxylic acid dichloride STR39 2,6-Naphthalenedicarboxylic acid (0.5 g) was added to 10 ml of thionyl chloride, and N,N-dimethylformamide in a very small amount was added to the mixture. The resulting mixture was refluxed for 4 hours. The unaltered thionyl chloride was removed by evaporation to give the desired compound (0.48 g).
With thionyl chloride; In toluene;
The naphthalene-2,6-dicarboxylic acid chloride used as the starting material was prepared as follows: A mixture of 1 g of naphthalene-2,6-dicarboxylic acid and 100 ml of toluene was treated with 2 ml of thionyl chloride under a nitrogen atmosphere and subsequently heated under slight reflux overnight. The reaction mixture was concentrated, then treated with 50 ml of absolute toluene and again concentrated. This procedure was repeated twice. Subsequently, the solid residue was sublimed in a bulb tube. This gave 0.8 g of naphthalene-2,6-dicarboxylic acid chloride.
With thionyl chloride;
1) 2,6-naphthalene dicarboxylic acid chloride STR29 2,6-naphthalene dicarboxylic acid (0.5 g) was added to 15 ml of thionyl chloride, and N,N-dimethylformamide in a very small amount was added to the mixture. The resulting mixture was refluxed for 4 hours. Unaltered thionyl chloride was removed by evaporation to give 0.45 g of the desired compound.
With thionyl chloride; for 4h;Reflux;
Example VII-IIIPreparation of Compound 204General Procedure VII-KNaphthalene-2,6-dicarboxylic acid (VII-IIIA) (2.2 g, 10.2 mmol) was dissolved in 20 mL of SOCl2 and the mixture was refluxed for 4 hrs. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was dissolved in 400 mL of acetone and was added into the solution of NaN3 (2.585 g, 39.73 mmol) in 50 mL of water at 0 C. The reaction was stirred at r.t. overnight. The precipitate formed was filtered, washed with water and dried to give compound VII-IIIB (2.48 g, yield 94%). 1H NMR (DMSO-d6, 400 MHz) δ 8.76 (s, 2H), 8.35 (d, J=8.8 Hz, 2H), 8.07 (d, J=8.4 Hz, 2H).
First, 80 g of 2,6-naphthalene dicarboxylic acid is dispersed in 400 g of phosphoryl chloride. The dispersion kept thoroughly stirred and 8 g of dimethyl formamide (DMF) gradually added thereto are refluxed together on a hot water bath for 2.5 hours. After the ensuing reaction has been completed, the reaction mixture is distilled to expel phosphoryl chloride by evaporation. The residue of this distillation is recrystallized from benzene to obtain as needle crystals 61 g (yield: 65%) of 2,6-dichloroformylnaphthalene (melting point: 186 C.).
EXAMPLE 13 (Compound 13)2,6 dinaphtoxybenzamido-4,4'-phenoxyisobutyric Acid; A mixture of 2.225 g (0.01 mole) 2-6 naphthalenedicarboxysilic acid, 25 ml tetrahydrofuran (THF) and 2.2 ml (0.02 mole) triethylamine is cooled in a freezer and then 2.75 ml (0.02 mole) benzylchoroformate is added with stirring. This ice cooled product is added to 3.9 g <strong>[117011-70-8]4-aminophenoxyisobutyric acid</strong> and dissolved in a solution of 1 g sodium hydroxide in 5 ml water cooled. The mixture is stirred at room temperature and then evaporated at room temperature (air) to remove THF. It is then acidified with acetic acid and 2.2 g of starting dicarboxylic acid as white powder is recovered. The structure is structure13. C32H30N2O8mw 570 mp greater than 300 C. The above compound is also made using ethylchoroformate instead of benzylchloroformate giving 60% yield.
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