Asymmetric dioxime ester compound, making method and application thereof
A technology of compounds and general formulas, applied in applications, oxime preparation, thioether preparation, etc., can solve the problems of increased molecular weight, low activity of oxime esters, and no improvement in photosensitivity
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Example Embodiment
[0128] Example 1 Synthesis of 5-phenylthioindan-1-one
[0129]
[0130] Weigh 33.3g (0.2mol) 5-chloro-1-indanone in a 50ml three-necked flask, add 30ml N,N-dimethylformamide (DMF), 30.0g (0.27mol) thiophenol, 36g anhydrous carbonic acid Potassium, nitrogen protection, stirring at 40-45℃ for 6h; Recover DMF under reduced pressure, add the residue to 100ml water, extract twice with 25ml 1,2-dichloroethane, combine the 1,2-dichloroethane solution, use Wash twice with 10ml water, spread filter paper in a Buchner funnel, use it to filter the organic phase, concentrate the filtrate to dryness, and recrystallize the residue with methanol. After drying, 43.4g of light yellow crystals are obtained. The yield is 90.3%. The purity is analyzed by HPLC. 98.2%. The melting range is 46.0-48.0℃.
Example Embodiment
[0131] Example 2 Synthesis of 5-(4-octanoylphenylthio)indan-1-one
[0132]
[0133] Weigh 24.04g (0.1mol) of the product 5-phenylthioindan-1-one of Example 1 and dissolve it in 120ml of 1,2-dichloroethane, reduce the temperature to 5-10℃, and add 28g (0.21mol) of anhydrous Aluminum trichloride, 17.9g (0.11mol) octanoyl chloride was added dropwise with stirring, after the addition, stirred for 4h, treated the reaction liquid with dilute hydrochloric acid, separated the organic solution, washed again with water, concentrated to recover 1,2-dichloroethane, The residue was recrystallized in 100ml ethanol to obtain 33.1g of white crystals, yield 90.1%, melting range 74.3-75.2℃, 1 H-NMR data indicated that the product obtained was 5-(4-octanoylphenylthio)indan-1-one; 1 H-NMR(CDCl 3 ), δ(ppm) value data: 0.8848(t,3H,CH 3 ), 1.2892-1.3412(m,8H,4CH 2 ), 1.7359(m,2H,CH 2 ), 2.7066(t,2H,c-CH 2 ), 2.9526(t,2H,CH 2 ), 3.0961(t,2H,c-CH 2 ), 7.2740 / 7.3008(d,1H,ArH), 7.3734(s,1H,ArH), 7.4525 / 7.47...
Example Embodiment
[0134] Example 3 Synthesis of 5-(4-octanoylphenylthio)indan-1,2-dione-2-oxime
[0135]
[0136] Take 18.4g (0.05mol) of 5-(4-octanoylphenylthio)indan-1-one obtained in Example 2 and dissolve it in a 250ml three-necked flask with 150ml of ethanol, add 2g of 36% concentrated hydrochloric acid, water bath 15 Keep the temperature at -20℃ and stir. Add 6.2g (0.06mol) n-butyl nitrite dropwise within 15min. After stirring at 25℃ for 5h, the reaction solution will be cooled to 5-10℃. The precipitated yellow solid will be filtered. After drying, 18.7g will be analyzed. 98.90%, melting range 162.7-164.0℃, 1 H-NMR data indicated that the product obtained was 5-(4-octanoylphenylthio)indan-1,2-dione-2-oxime with a yield of 94.2%; 1 H-NMR(CDCl 3 ), δ(ppm) value data: 0.8866(t,3H,CH 3 ), 1.2965-1.3512(m,8H,4CH 2 ), 1.7493(m,2H,CH 2 ), 2.9737(t,2H,CH 2 ), 3.7977(s,2H,c-CH 2 ), 7.2674 / 7.2943(d,1H,ArH), 7.3320(s,1H,ArH), 7.5281 / 7.5558(d,2H,2ArH), 7.7707 / 7.7977(d,1H,2ArH), 7.9648 / 7.9925(d, 2H, 2ArH...
PUM
Property | Measurement | Unit |
---|---|---|
Thickness | aaaaa | aaaaa |
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap