Single isomeric conjugates of rhodamine dyes
A dye and isomerization technology, applied in the field of novel rhodamine dyes, can solve the problems of double reactivity difficult to establish a reliable single isomer product method, isomer ratio change, product influence and other problems
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[0062] Solvents and reagents were used as received from Labscan (Gliwice, Poland) and Sigma-Aldrich (St. Louis, MO), respectively. A liquid chromatography-mass spectrometry (LCMS) system from Agilent Technologies (Santa Clara, CA) consisting of a G1379B degasser, G1312A binary pump, G1329A autoinjector, G1316A column was used. Type heating furnace, G1365BUV-Vis detector (used to detect the maximum absorbance) and 6110 quadrupole MS detector. Purity was measured by high-performance liquid chromatography (HPLC) with an ACE-C8 column (50 x 4.6 mm) maintained at 35°C, and with 10% to 97% acetonitrile in 0.1% trifluoroacetic acid (TFA) for 3 minutes Gradient elution.
[0063] Compounds in the Examples below are named based on Marvin Sketch 5.2.6, where structures are named using preferred IUPAC naming conventions. However, other nomenclature systems may be used to name these compounds.
example 1
[0064] Example 1: Preparation of Intermediate 1
[0065] The following compounds were prepared:
[0066]
[0067] Intermediate 1
[0068]8-Hydroxyjulolidine (1.1 g, 5.8 mmol) and sodium 2-formylbenzene-1-sulfonate (0.6 g, 2.9 mmol) were stored in 60% H 2 SO 4 The reaction mixture in aqueous solution (10 mL) was stirred at 150 °C under air atmosphere for 2 hours, after which time the starting material had been completely converted to the expected product. The pH of the reaction was adjusted to about 7 with 60% aqueous NaOH, and the product was expected to precipitate during this procedure. The precipitate was filtered and washed with toluene (3 x 50 mL) and dried in vacuo. The crude product was dissolved in warm ethanol (EtOH) and filtered. The insoluble solid was discarded and the filtrate was evaporated in vacuo with toluene (3 x 50 mL) and 1.1 g of the title molecule was obtained in 90% HPLC purity and 73% yield.
example 2
[0069] Example 2: Preparation of Intermediate 2
[0070] The following compounds were prepared:
[0071]
[0072] Intermediate 2
[0073] 8-Hydroxyjulolidine (1.4 g, 7.2 mmol) and 4-formylbenzoic acid (500 mg, 3.6 mmol) were mixed with 60% aqueous sulfuric acid (40 mL), and stirred at 150° C. for 24 hours in an air atmosphere . The reaction mixture was added to ice (100 g), after which 60% NaOH was carefully added to pH 6-7, causing the crude product to precipitate. The crude product was extracted between dichloromethane (DCM) and water. The organic phase was separated and washed with brine. The organic solvent was removed and the final product was dried by co-evaporating with EtOH and toluene five times to give 1.1 g of product (61% yield). Purity was determined to be 100% by HPLC. MS(ESI)[M+]=491.
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