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α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
157.6 g
With hydrogenchloride; aluminum (III) chloride; water; In nitromethane; at 10 - 20℃; for 16.0h;
Add to a 1000 mL reaction flask300 mL of nitromethane,Adding 203 g of anhydrous aluminum trichloride in portions, After cooling to room temperature, add 114g aminoacetonitrile hydrochloride; to a temperature below 20 C, 150 g of intermediate III (<strong>[123664-84-6]4-phenoxy-3-methanesulfonamidoanisole</strong>) was added; after stirring for 10 minutes, a dry hydrogen chloride gas was introduced, Ventilation for about 15h, the end of the reaction. The reaction solution was slowly added to 1200 g of 2 mol / L dilute hydrochloric acid at a controlled temperature of 10 C or less, for stirring 1h, filter, solid with a small amount of water (about 80mL) washing, drying; and then 150mL ethyl acetate beating, filter dry,Dry; then the solid and then twice the volume of 95% (volume percentage) of ethanol reflux lh cooling, filtration, solid bake to moisture qualified,157.6 g of the final product (alpha-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride), 105.07% by weight, and a purity of 99.49% For 168.8 to 17.1.4 C.
α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride[ No CAS ]
[ 149456-98-4 ]
Yield
Reaction Conditions
Operation in experiment
93.56%
Stage #1: formic acid; sodium formate With pivaloyl chloride In acetone at 18 - 20℃; for 1h; Large scale;
Stage #2: α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride In acetone at 10 - 20℃; for 3h; Large scale;
5 A method for preparing an elamolide formylation intermediate, comprising the steps of:
General procedure: (A)1.43 kg of formic acid and 2.64 kg of sodium formate were added to 30 L of acetone.Stir at 18-20 ° C, after the dispersion is uniform, add 3.74 kg of pivaloyl chloride.Stirring the reaction for 1 h to obtain a mixed acid anhydride system;(B)To the reaction system obtained in the step (A), 12.02 kg of 2-amino-1-(2-methoxy-4-methanesulfonamido-5-phenoxy)phenylethanone hydrochloride (Compound I) was added. And 2.64 kg of sodium formate, the temperature is controlled at 10-20 ° C, and the reaction is stirred for 3 h to terminate the reaction;(C)The temperature of the system obtained in the step (B) is lowered by 10 ± 5 ° C under stirring conditions.Slowly add water and keep the temperature during the addition of water not exceeding 20 °C.After the end of the watering, the temperature is controlled to 15±5°C, and after stirring for 1 hour, it is filtered.The filter cake is washed with water to collect the filter cake;The filter cake was recrystallized by heating under reflux with 20 L of acetonitrile.After cooling to 10-25 ° C for crystallization, the solid was collected by filtration.An off-white solid gave an off-white solid.
1-3
Dissolve 1.02g of formic acid in 50ml of dichloromethane, add to a 250ml three-necked flask and stir, control the temperature at 15-25°C,Add 5.28g (1.5eq) of N,N-carbonyldiimidazole (CDI) in batches, stir for 1h after adding,The system is dissolved, and under the condition of 15-25°C,Add 8.40g (1.0eq) 2-amino-1-(2-methoxy-4-methanesulfonamido-5-phenoxyphenyl)ethanone hydrochloride (4) in batches,After reacting for 1-2h, TLC monitors the complete reaction of the raw materials. Add 50ml purified water and 50ml dichloromethane to the reaction system, stir for 30min, and separate into layers.The organic phase was concentrated to dryness under reduced pressure, and 50 ml of isopropanol was added to make a slurry for 30 minutes, and then filtered with suction to obtain compound 1 (7.54 g, 91.7%) with a purity of 99.95%.
α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride[ No CAS ]
[ 149456-98-4 ]
Yield
Reaction Conditions
Operation in experiment
67.4%
Stage #1: sodium formate With pivaloyl chloride In acetone at 25℃; for 4h;
Stage #2: α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride In acetone at 25℃; for 5h;
4
Add 19.77g acetone and 3.14g pivaloyl chloride to a 250mL three-necked flask, turn on magnetic stirring, control the temperature to 25±5°C, add 4.42g anhydrous sodium formate, and stir for 4h.Weigh 8.40g 2-amino-1-(2-methoxy-4-methanesulfonamido-5-phenoxyphenyl)ethanone hydrochloride and add it to a three-necked flask, and control the temperature to 25±5°C , Reaction for 5h, sampling TLC monitoring.After the completion of the reaction, 84.00g of purified water was added to the three-necked flask, stirred for 30±5min, filtered with suction, and the filter cake was washed once with 16.80g of purified water.The filter cake was added to a three-necked flask, 13.20 g of isopropanol was added, stirred for 60 min, and filtered with suction to obtain an off-white solid, which was compound 1 (5.66 g, 67.4%) with a purity of 88.23%.
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