Preparation method of imrecoxib and intermediate thereof
A technology of intermediates and compounds, applied in the field of drug synthesis, can solve the problems of difficult control and research of raw material impurities, high toxicity of operation process and waste water, and increased difficulty of separation of target products, so as to avoid heavy metal oxidizing reagents and no pollutants The effect of producing and reducing production costs
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Embodiment 1
[0051] A) Preparation of N-[2-oxo-2-(4-methylsulfonylphenyl)]ethyl-4-methylphenylacetamide (compound (Ⅲ)):
[0052] 2-Amino-1-p-methylsulfonylacetophenone (10.0g, compound (I)) was dissolved in acetonitrile (60mL), added triethylamine (7.1g), stirred and cooled to 5-10°C in an ice bath, dropwise Add p-methylphenylacetyl chloride (9.5g, compound (Ⅱ), X 1 Chlorine) in acetonitrile (15mL) solution, warmed up to 40°C and reacted for 12h until the reaction was complete, cooled to room temperature, adjusted to neutral with 1N hydrochloric acid, removed the organic solvent by rotary evaporation under reduced pressure, added ethyl acetate and water for extraction, and separated The organic phase was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, concentrated to dryness by rotary evaporation under reduced pressure, and the obtained crude product was recrystallized with ethanol to obtain N-[2-oxo-2-(4-methylsulfonylphenyl )] Ethyl-4-methylpheny...
Embodiment 2
[0058] A) Preparation of N-[2-oxo-2-(4-methylsulfonylphenyl)]ethyl-4-methylphenylacetamide (compound (Ⅲ)):
[0059] 2-Amino-1-p-methylsulfonylacetophenone (18.0g, compound (I)) was dissolved in methyl tert-butyl ether (100mL), N,N-diisopropylethylamine (27.3g) was added, Stir and cool in an ice bath to 5-10°C, add p-methylphenylacetyl bromide (27.0g, compound (II), X 1 bromine) in methyl tert-butyl ether (50mL) solution, heated to 20°C, reacted for 16h until the reaction was complete, adjusted to neutral with 1N hydrochloric acid, removed the organic solvent by rotary evaporation under reduced pressure, added ethyl acetate and water for extraction, The organic phase was separated, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, concentrated to dryness by rotary evaporation under reduced pressure, and the obtained crude product was recrystallized with ethanol to obtain N-[2-oxo-2-(4-methylsulfonyl Phenyl)]ethyl-4-methylphenylacetamide, ...
Embodiment 3
[0065] A) Preparation of N-[2-oxo-2-(4-methylsulfonylphenyl)]ethyl-4-methylphenylacetamide (compound (Ⅲ)):
[0066] 2-Amino-1-p-methylsulfonylacetophenone (20.0g, compound (I)) was dissolved in chloroform (110mL), added pyridine (14.8g), stirred and cooled to 5-10°C in an ice bath, and added dropwise to Toluyl acetyl chloride (20.6g, compound (Ⅱ), X 1 Chloroform (30 mL) solution of chlorine) was raised to 60°C for 6 hours until the reaction was complete, then cooled to room temperature, adjusted to neutrality with 1N hydrochloric acid, removed the organic solvent by rotary evaporation under reduced pressure, added ethyl acetate and water for extraction, and separated The organic phase was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, concentrated to dryness by rotary evaporation under reduced pressure, and the obtained crude product was recrystallized with ethanol to obtain N-[2-oxo-2-(4-methylsulfonylphenyl )] Ethyl-4-methylphenylac...
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