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[ CAS No. 119018-29-0 ] {[proInfo.proName]}

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Chemical Structure| 119018-29-0
Chemical Structure| 119018-29-0
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Product Details of [ 119018-29-0 ]

CAS No. :119018-29-0 MDL No. :MFCD02955393
Formula : C16H21N3O4S Boiling Point : -
Linear Structure Formula :- InChI Key :AJEMFZRCUKJSES-UHFFFAOYSA-N
M.W : 351.42 Pubchem ID :11772520
Synonyms :
Chemical Name :4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide

Safety of [ 119018-29-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 119018-29-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 119018-29-0 ]

[ 119018-29-0 ] Synthesis Path-Downstream   1~14

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  • [ 599174-27-3 ]
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  • 2
  • [ 119043-16-2 ]
  • [ 119018-29-0 ]
YieldReaction ConditionsOperation in experiment
97.8% With ammonia; In water; at 80℃; for 1.5h; 120 g of chlorosulfonic acid was added to a three-necked bottle, and the compound m was added in portions. After the addition, the reaction was kept at 80 C for 0.5 hour. The reaction was completely monitored by TLC, and the temperature was lowered to 25 C. The reaction was dropped into ice water and filtered to obtain a solid. Adding solid to a solution of 200 ml of ammonia water and 100 ml of water, heating to 80 C for 1.5 hours, cooling to 30 C, adding hydrochloric acid to the reaction solution, separating the solid, filtering, washing with water, drying at 50 C, The obtained white solid was 25.2 g, and the purity by HPLC was 78.08%, the impurity V 7.24%, the impurity was 16.35%, and the yield was 97.8%.
With ammonia; at 70℃; for 3 - 4h; Example 2Preparation of 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl ] benzene sulfonamide (IV)3-Ethyl-4-methyl-2,5-dihydro-lH- pyrrole-2-one (II) (1.0 Kg) and beta-phenylethyl isocyanate (1.488 Kg) were mixed in anhydrous toluene (4.0 L) and refluxed for 4 hrs. The toluene was distilled off and hexane (8.0 L) was added to the reaction mixture at 5O0C. The product precipitated is cooled to 0 to 5 C to obtain the solid compound viz. 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene (2.17 Kg). It was filtered & washed with 2.0 L of hexane.To a cooled (15 to 25 C) solution of chlorosulfonic acid (2.8 L), 4-[2-(3-Ethyl-4- methyl-2-carbonyl pyrrolidine amido) ethyl] benzene (2.0 Kg) was added in small portions over a period of 2 to 3 hrs. Further it was stirred for 30 min at this temperature and then temperature was gradually raised to 30 to 350C. The reaction mass is stirred further for 2 hrs. The reaction mixture was then quenched into ice- water and stirred for 1 hr and filtered to obtain the product 4-[2-(3-Ethyl-4-methyl-2- carbonyl pyrrolidine amido) ethyl] benzene sulfonyl chloride (2.0 kg). To a cooled (15 to 200C) solution of diluted ammonia (1.4 L) 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonyl chloride was added in small portion over 1 to 2 hrs. The reaction mixture was then heated to 7O0C for 2 hrs when ammonolysis is complete. The product converted is then stirred for 1 hr at R.T. and filtered and dried at 90. to 100 C to obtain crude 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide (2.2 Kg) having HPLC purity in the range of 82 to 88%. The crude compound 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide (2.2 Kg) is then purified from mixture of organic solvents chosen from Methanol, Acetone & toluene.
8.47 kg With ammonium hydroxide; In methanol; at 20 - 30℃; for 2h;Industrial scale; 38.0 kg of methanol was sequentially added to a 100 L reactor.Industrial ammonia water 5.1Kg; start stirring,Add the above intermediate 2 crude wet product at 20-30 C,And the reaction was kept for 2 hours; the sample was controlled by HPLC, and the reaction was completely filtered and washed with water.The obtained white intermediate 3 crude wet product was directly charged into another 200 L reaction kettle.Further, 110.0 kg of methanol was added, and the temperature was raised to 65-75 C, and the mixture was stirred for 4 hours.Cool down to 20-25 C, filter,Drying white solid intermediate 3 refined product 8.47kg, HPLC purity >99%,The meta isomer impurity was 0.2 <%, and the molar yield was 64% (based on the intermediate 1).
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  • [ 766-36-9 ]
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  • [ 61892-80-6 ]
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  • 5
  • [ 247098-17-5 ]
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  • 6
  • [ 607-97-6 ]
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  • trans-hydroxyglimepiride [ No CAS ]
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  • cis-hydroxyglimepiride [ No CAS ]
  • 10
  • [ 541-41-3 ]
  • [ 119018-29-0 ]
  • C19H25N3O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine; In dichloromethane; at 5 - 30℃; Examples: Example 1: Preparation of carbamate of Formula IX (R'= ethyl, and Grp1=D) In a reaction vessel 100 gm of 4[2-(3-ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide, 72 gm triethyl amine and 1.6 lit dichloromethane were taken and the mixture cooled to 0 C. 46.15 gm of ethyl chloroformate was diluted separately with 200 ml dichloromethane and added into the reaction vessel drop wise while maintaining the temperature at around 5 C and maintained for 2 hours at 5 C and then at 25 to 30 C till completion of reaction. 2 L water and 0.7 L dichloromethane was added and the pH of the reaction mass were adjusted to 4 by addition of acetic acid. The organic layer was separated and washed with water and concentrated to dryness. The residue was refluxed with 300 ml acetone and cooled to 25 to 30 C, maintained for 1 hour, filtered and washed with 100 ml chilled acetone to get 100 gm carbamate of Formula IX (yield 83percent, purity 99.7percent). Melting Point: 177 to 182 C
83% With triethylamine; In dichloromethane; at 0 - 30℃; for 2h; In a reaction vessel 100 g of 4[2-(3-ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide, 72 g triethyl amine, and 1.6 L of dichloromethane were mixed and cooled to 0° C. 46.15 g of ethyl chloroformate was diluted separately with 200 mL of dichloromethane and added into the reaction vessel drop wise while maintaining the temperature at around 5° C. for 2 hours, and then at 25 to 30° C. until completion of the reaction. 2 L of water and 0.7 L of dichloromethane were added; and the pH of the reaction mass was adjusted to 4 by addition of acetic acid. The organic layer was then separated, washed with water, and concentrated to dryness. The residue was refluxed with 300 mL of acetone and cooled to 25 to 30° C., maintained for 1 hour, filtered, and washed with 100 mL of chilled acetone to obtain 100 g carbamate of Formula IX (yield 83percent, purity 99.7percent, and melting point: 177 to 182° C.).
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  • trans-4-methyl cyclohexyl isocyanate [ No CAS ]
  • [ 119018-29-0 ]
  • [ 93479-97-1 ]
YieldReaction ConditionsOperation in experiment
~ 50% 4- [2- (3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide(100g) was dissolved in tetrahydrofuran (1800 ml) by stirring and gradually heating to reflux. The reaction mixture was cooled to50-55 C and dryK2CO3 (61 g) was added to it and heated gradually to reflux and maintained for 6 hours. Approximately 300 ml of solvent was distilled of from the reaction mixture during this time.Trans-4-methylyclohexyl isocyanate(221g) in toluene (24.46percent w/w) was added to the reaction mixture at reflux temperature in 5-10 minutes. The reaction mixture was refluxed for 6 hours and then cooled to40-45 C and filtered at this temperature. The product was washed with tetrahydrofuran (300 ml) and suck dried for 30 minutes. Then it was taken into DM water(2000ml) and stirred for 15 min at25-30 C, the pH was adjusted to 6-6.5 withHC1 solution (130 ml, 1: 1) and stirred for 30 minutes at20-25 C. Then pH was brought to 8- 8.5 by drop wise addition of 5percent aq KOH solution (about 20 ml) and stirred for 30 minutes at25-30 C. The product was filtered and washed with water (400 ml), followed by methanol (20 ml), suck dried and slurried in water (2000 ml) for 1 hour at45-50 C and filtered. The wet cake was slurried in toluene (1000 ml) for 1 hour at 80-85 C, cooled and filtered, washed with toluene, followed by methanol to obtain glimepiride, wet weight: 200g (moisturecontent-50percent).
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  • [ 32175-00-1 ]
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  • [ 93479-97-1 ]
YieldReaction ConditionsOperation in experiment
94.5% In tert-butyl methyl ether; cyclohexanone; at 30℃; for 10h; 2-(3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethylbenzenesulfonamide (F) prepared in Example 5 (2.6 g, 1.37 mol )After being mixed with trans-p-methylcyclohexyl isocyanate (G) (2.1 g, 1.64 mol), it was dissolved in a mixture of cyclohexanone (45 ml) and methyl tert-butyl ether (30 ml), and heated to 30°C in a water bath. ,After stirring for 10 hours, the heating was stopped, and the mixture was naturally stirred and cooled to 10° C., poured into water, extracted with dichloromethane (90 ml), concentrated, dissolved in ethanol, and crystallized at 3° C.Dry to give 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-3 -(trans-4-methylcyclohexyl)-urea (H) (3.74 g), yield 94.5percent, purity 99.82percent.
86.3% Example 4Preparation of 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans;-4-methyl cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo- 1 H-pyrrole- 1 - carboxamide (I).In a reaction vessel containing (24.2 L) Acetone, 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide (1.0 Kg) and potassium carbonate (0.46 Kg) was added and refluxed at about 55 to 60 C for 1 hr. trans-4-Methyl- cyclohexyl isocyanate was obtained by method known in art from trans-4-methyl- cyclohexylamine. A solution of trans-4-methyl-cyclohexyl isocyanate (0.515 Kg) in toluene (5 L) was prepared and added to the above reaction mixture. This reaction mixture is refluxed for 12 lirs, then cooled. To this cooled reaction mass charge 27 L of water. The reaction mass was filtered and the pH was adjusted to 5.5 to 6.0 by adding acetic acid at about 20 to 250C. The solid obtained was filtered and washed with water. The 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(/7-?ro-4-methyl cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-lH-pyrrole-l- carboxamide (I) obtained is then dried at 90 to 1000C till constant weight. Yield of the product is 86.3percent. Example 5Purification of 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(tr?ro-4-methyl cyclohexyl)amino] carbonyl] amino] sulfonyljphenyl] ethyl] -2-oxo- 1 H-pyrrole- 1 - carboxamide (I)In a reaction vessel containing 6.0 L methanol and 1.0 Kg crude Glimepiride, dry ammonia gas was purged at 20 to 25 C till all Glimepiride dissolves and a clear solution is obtained. This homogeneous mass was then charcoalised, filtered and finally neutralized with Glacial acetic acid to pH 5.5 to 6.0, till the entire product precipitates out. The pure Glimepiride was then filtered and dried at 65C to 700C till constant weight. Yield obtained was ~ 90percent.
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  • [ 210827-31-9 ]
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  • 3-ethyl-N-(4-(N-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)carbamoyl)sulfamoyl)phenethyl)-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide [ No CAS ]
  • 14
  • phenyl 3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate [ No CAS ]
  • [ 35303-76-5 ]
  • [ 119018-29-0 ]
YieldReaction ConditionsOperation in experiment
85% In tetrahydrofuran; at 20℃; 3-Ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate(1; 1.349 g, 5.5 mmol) and 4-(2-aminoethyl)benzenesulfonamide(1.001 g, 5 mmol) were dissolved in THF (40 mL), and themixture was stirred at r.t. over night. After completion of thereaction (TLC), the solvent was evaporated under reduced pressure,and the crude product was purified by crystallization(EtOAc) to give a white solid yield: 1.495 g, (85%); mp 183-185 C.1H NMR (400 MHz, DMSO-d6): delta = 8.37 (t, J = 5.2 Hz, 1 H), 7.45(d, J = 7.8 Hz, 2 H), 7.43 (d, J = 7.8 Hz, 2 H), 7.32 (s, 2 H), 4.17 (s, 2H), 3.49 (q, J = 6.0 Hz, 2 H), 2.88 (t, J = 6.5 Hz, 2 H), 2.18 (q, J = 7.3Hz, 2 H), 2.01 (s, 3 H), 0.97 (t, J = 7.4 Hz, 3 H). 13C NMR (100MHz, DMSO-d6): delta = 172.3, 152.5, 152.1, 143.8, 142.6, 132.3,129.5, 126.2, 52.3, 40.6, 35.5, 16.4, 13.3, 13.2. HRMS (ESI): m/z[M + Na]+ calcd for C16H21N3NaO4S: 374.1150; found: 374.1140.
85.5% In isopropyl alcohol; for 6h;Reflux; The compound Kappa 5.0g, 4-(2-aminoethyl)benzenesulfonamide 4.08g and isopropanol 50g were heated under reflux for 6 h (4-(2-aminoethyl)benzenesulfonamide remaining 0.79%), cooled to After drying at 25 C, filtration and 50 C, 6.12 g of compound I was obtained. The purity of the solution was 98.66% by HPLC, the impurity was 0.60%, and the impurities V and VI were not detected. The yield was 85.5%.
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