4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide Chemical Properties

Melting point:

177-179?C

Density 

1.304

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

10.16±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C16H21N3O4S/c1-3-14-11(2)10-19(15(14)20)16(21)18-9-8-12-4-6-13(7-5-12)24(17,22)23/h4-7H,3,8-10H2,1-2H3,(H,18,21)(H2,17,22,23)

InChIKey

AJEMFZRCUKJSES-UHFFFAOYSA-N

SMILES

N1(C(NCCC2=CC=C(S(N)(=O)=O)C=C2)=O)CC(C)=C(CC)C1=O

CAS DataBase Reference

119018-29-0(CAS DataBase Reference)

Safety Information

Risk Statements 

52/53

Safety Statements 

61

HS Code 

2935909550

4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide Usage And Synthesis

Chemical Properties

White Solid

Uses

4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide (Glimepiride EP Impurity B) is an intermediate for the preparation of Glimepiride.

Synthesis

38.0 kg of methanol and 5.1 kg of industrial ammonia were sequentially added to a 100 L reactor and stirring was initiated. The crude wet product of Intermediate 2 was added slowly at 20-30°C and the reaction was maintained for 2 hours. The progress of the reaction was monitored by HPLC and after the reaction was complete, filtration was carried out and the filter cake was washed with deionized water. The obtained crude wet product of white Intermediate 3 was directly transferred to a 200 L reactor. Subsequently, 110.0 kg of methanol was added, the reaction temperature was raised and stirring was continued for 4 hours. After completion of the reaction, the mixture was cooled to 20-25 °C, the product was separated by filtration and dried to obtain 8.47 kg of white solid Intermediate 3 refined product, with purity >99% and interstitial isomer impurity content of 0.2% by HPLC.

References

[1] Tetrahedron Letters, 2003, vol. 44, # 26, p. 4853 - 4855
[2] Patent: WO2006/103690, 2006, A1. Location in patent: Page/Page column 7,14-15
[3] Patent: CN108383768, 2018, A. Location in patent: Paragraph 0101; 0102

4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide(119018-29-0)Related Product Information

• Formamide
• Formamide,Deionized
• Kresoxim-methyl
• METSULFURON METHYL
• Tribenuron methyl
• N-Ethylmethylamine
• PHENYL VALERATE
• Benzamide
• Chlorantraniliprole
• Methyl acetate
• N,N-Dimethylformamide
• Methyl salicylate
• Thiophanate-methyl
• Methyl
• [[4-[2-[[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)carbonyl]amino]ethyl]phenyl]sulfonyl]-carbamic acid ethyl ester
• Glimepiride
• Phenethyl isocyanate
• 3-Ethyl-2,5-Dihydro-4-Methyl-2-Oxo-N-(2-Phenylethyl)-1h-Pyrrole-1-Carboxamide