N-[2-[4-(Aminosulfonyl)Phenyl]Ethyl]-3-Ethyl-4-Methyl-2-Oxo-1H-Pyrrole-1-Carboxamide
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HS Code |
616829 |
| Chemical Formula | C18H21N3O4S |
| Molar Mass | 375.44 g/mol |
As an accredited N-[2-[4-(Aminosulfonyl)Phenyl]Ethyl]-3-Ethyl-4-Methyl-2-Oxo-1H-Pyrrole-1-Carboxamide factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of N -[2 -[4 -(Aminosulfonyl)phenyl]ethyl]-3 -ethyl -4 -methyl -2 -oxo -1H -pyrrole -1 -carboxamide in sealed container. |
| Shipping | The chemical "N-[2-[4-(Aminosulfonyl)phenyl]ethyl]-3 -Ethyl-4 -Methyl-2 -Oxo-1H -Pyrrole-1 -Carboxamide" will be shipped in sealed, specialized containers, following strict chemical transport regulations to ensure safety during transit. |
| Storage | Store the chemical “N-[2-[4-(Aminosulfonyl)phenyl]ethyl]-3-ethyl-4-methyl-2-oxo-1H-pyrrole-1-carboxamide” in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent moisture absorption and potential reaction with air components. Ensure proper ventilation in the storage area to minimize risks. |
Why do industrial-scale azo condensation reactions stall at sulfonamide coupling components without pH-stat control?Production of high-performance bisacetoacetarylide and pyrazolone-free C.I. Pigment Orange and C.I. Pigment Red grades via the condensation of N-[2-[4-(aminosulfonyl)phenyl]ethyl]-3-ethyl-4-methyl-2-oxo-1H-pyrrole-1-carboxamide with 3,3′-dichlorobenzidine-based tetrazonium salts requires precise maintenance of coupling pH at 4.8–5.3 with automated metering of 2.5 M sodium acetate. Deviation beyond ±0.2 pH units shifts the reaction toward mono-coupling and destroys the symmetrical bis-azo chromophore, resulting in a hypsochromic shift exceeding 45 nm and a tinctorial strength loss of ≥28% against the reference standard. In a 5,000 L baffled glass-lined reactor equipped with a pH probe and iterative feed-forward control, the intermediate slurry is coupled at 0–2°C, held for 4 h, then heated to 95°C to complete ring-closure of the pyrrole-carboxamide bridge, yielding an insoluble crude presscake. After membrane filter-pressing and washing to conductivity <150 μS/cm, the paste is kneaded in a twin-shaft Z-blade mixer with 18–22 wt% water, 2.0 wt% rosin-modified maleic resin (acid number 110–130 mg KOH/g), and 0.5 wt% sodium dodecylbenzenesulfonate at 60°C for 6–8 h to induce controlled crystal ripening into the β-modification. Finished presscake is dried in a conical vacuum dryer at 80°C<50 mbar until moisture <0.5% and milled to an agglomerate size D₅₀ ≤ 0.6 µm. Formulated automotive OEM basecoat incorporating this pigment at 6.2±0.3 wt% on total binder solids must pass ISO 28199-7:2013 rub resistance and ISO 20566:2013 car-wash scratch testing, with ΔE* ≤ 1.0 after 2,000 h Xenon-arc exposure per SAE J2527. Terminal product is a high-chroma, weatherable red-shade orange for solventborne refinish systems and waterborne mono-coat finishes.
Transfer ribbon dye layer formulation thresholds and PET back-coating compatibilityWhen the title compound is employed as a sublimable thermal transfer dye in near-edge wax/resin ribbon architectures, differential scanning calorimetry of the raw dye must exhibit a sharp melt endotherm with onset ≥ 178°C and a 5% mass-loss temperature exceeding 295°C under N₂ by ASTM E2550-21; any lot exhibiting a secondary endotherm below 160°C triggers automatic rejection due to pre-transfer ghosting during 60°C shipping storage. The dye is pre-dispersed via a horizontal bead mill (chamber volume 0.5 L, 0.3 mm yttria-stabilized zirconia beads, fill level 80%) in a vehicle consisting of poly(vinyl butyral) (Mw 40,000–60,000, hydroxyl content 18–20%), hydrocarbon wax (C₃₅–C₄₀ normal paraffin, congealing point 78–82°C), and methyl ethyl ketone/toluene 60:40 w/w. In-process particle sizing via dynamic light scattering must remain within D₉₀ < 180 nm after 12 passes; recirculation beyond 18 passes without reaching the target indicates incomplete primary crystal breakage and requires a surfactant reformulation. The millbase is let down to a final coating fluid containing 3.2–4.0 wt% of the pyrrole carboxamide derivative on dry solids and applied to a 4.5-µm polyester film via a comma-reverse gravure coater at 120 m/min with a wet film thickness of 8–10 µm and three-zone flotation drying at 70/90/70°C. A back-coat based on silicone-modified polyurethane (dynamic coefficient of friction ≤0.25 per ISO 8295:2004 against a thermal head) is applied simultaneously. Finished jumbo rolls are slit to 110 mm-wide ribbons and must endure a 100,000-print durability test on a Zebra ZT411 thermal printer at print speed 8 ips, with bar code verification grade maintaining ANSI X3.182 Grade B or better throughout. End-use product is a high-density bar code label for logistics and cold-chain tracking that must withstand -25°C storage without dye crystallization. The substrate adhesion is validated under FINAT FTM-1 peel adhesion test. Starting with a 20,000 L sulfamic acid sulfonation train, 4-aminobenzenesulfonamide is alkylated with ethylene oxide under strictly anhydrous conditions (KF water <100 ppm) to generate 4-(2-hydroxyethyl)benzenesulfonamide, which is subsequently reacted with ethyl 3-ethyl-4-methyl-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate via a transamidation-distillation process at 165–175°C with continuous removal of ethanol. The resulting melt is quenched into deionized water at 4°C and crystallized from 25 vol% isopropanol to deliver the active pharmaceutical intermediate with chromatographic purity >99.3% by HPLC area percentage at 254 nm. This intermediate is not the final API but functions as the penultimate building block for a class of ATP-sensitive potassium channel modulators; in the subsequent step, 1.05 molar equivalents of cyclohexyl isocyanate are added to a 0.8 M solution in anhydrous dichloromethane containing 0.05 eq triethylamine and stirred at 22°C for 18 h under argon. The sulfonylurea formed is precipitated by solvent switching to n-heptane and recrystallized from acetone/water to produce a hypoglycemic agent conforming to the USP <621> chromatographic purity requirement of ≥99.8% and total impurities <0.5%. All manufacturing stages are executed in a dedicated ISO 8 cleanroom under ICH Q7 GMP for active pharmaceutical ingredient starting materials, with residual solvent levels (dichloromethane <600 ppm, n-heptane <5,000 ppm) controlled per Ph. Eur. 5.4. The end product is a scored tablet containing 2 mg or 4 mg of the sulfonylurea active for once-daily oral treatment of type 2 diabetes mellitus; bioequivalence is established per EMA/CPMP/EWP/QWP/1401/98 Rev.1.Electrophotographic charge transport layer doping: the regeneration threshold under positive corona cyclingIncorporation of N-[2-[4-(aminosulfonyl)phenyl]ethyl]-3-ethyl-4-methyl-2-oxo-1H-pyrrole-1-carboxamide as a secondary electron-transporting dopant into a bisphenol-A polycarbonate/ N,N′-diphenyl-N,N′-bis(3-methylphenyl)-(1,1′-biphenyl)-4,4′-diamine (TPD) matrix requires a precisely balanced molar doping ratio of 1.8–2.4 mol% relative to TPD; beyond 2.6 mol%, a steep increase in residual potential to >120 V after 5,000 corona cycles renders the photoreceptor drum non-functional in digital laser printers printing at 60 ppm. The single-layer organic photoconductor drum coating solution is prepared by dissolving 9.0 wt% polycarbonate (Mv 38,000, Tg 148°C) in tetrahydrofuran/cyclohexanone 70:30 w/w, adding the pyrrole carboxamide derivative and TPD under nitrogen blanket to maintain dissolved oxygen <1 ppm, and filtering through a 0.2 µm PTFE membrane before dip-coating aluminum cylinders (Ra<0.05 µm) at a withdrawal speed of 85 mm/min. Cured at 120°C for 60 min under forced convection to reduce residual solvent to <50 µg/cm², the layer must attain a thickness of 28±1 µm. Electrostatic cycling per ASTM F1443-20 at 23°C/50% RH with an initial charging voltage of -650 V and erasure wavelength of 780 nm defines the acceptance criterion: dark decay not exceeding 18 V/s and light-induced discharge to <-60 V within 0.2 s. Roll-out manufacturing validation includes a 200,000-print life test under ISO/IEC 19752:2017 monochrome toner yield protocol, requiring optical density variation <0.05. The terminal product is a long-life monochrome laser printer imaging unit rated for 30,000 pages at 5% coverage. Can a sulfonamide pyrrole chromophore replace benzotriazole UV absorbers in polyolefin greenhouse films while maintaining PAR transmittance?A twin-screw compounding trial on a ZSK 26 Mc18 co-rotating extruder (L/D 44, screw speed 400 rpm, throughput 15 kg/h) blending linear low-density polyethylene (LLDPE, MI₂1.0 g/10 min at 190°C/2.16 kg) with 0.25±0.02 wt% of the pyrrole carboxamide additive alongside a hindered amine light stabilizer (HALS) package of 0.15 wt% reveals a critical matter of processing: the compound melts at 191°C and must be metered via a side-feeder into the melt phase at barrel zone 6 to avoid premature sublimation loss exceeding 11% as measured by TGA off-gas analysis. Blown film (thickness 150 µm, blow-up ratio 2.8) produced on a 60 mm spiral mandrel die achieves a photosynthetically active radiation (PAR) transmittance of 88±1% between 400–700 nm and UV cutoff below 350 nm with less than 5% transmittance at 320 nm, assessed per EN 13206:2017 for covering films. Accelerated weathering per ISO 4892-3:2016 cycle 2 (wet/dry xenon-arc) demonstrates tensile strength retention at break of >80% after 8,000 h, with no detectable bromine or heavy metal migration into condensed water, meeting the indirect food contact requirements of EU 10/2011 Annex II for multilayer structures with a functional barrier endorsement. The final product is a three-layer greenhouse cladding film with a 36-month guaranteed lifespan in Mediterranean insolation, marketed under the EN 13206 conformity framework.
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| Parameter | Method / Standard | Typical Value or Limit |
|---|---|---|
| Appearance | Visual inspection | White to faint beige powder |
| Identification (1H NMR) | Bruker 400 MHz, DMSO-d6 | Consistent with assigned structure; characteristic NH2 singlet δ 7.2–7.4 ppm |
| Purity (HPLC) | Agilent 1260 Infinity II, C18 column, UV 254 nm, gradient H2O/MeCN + 0.1% TFA; integration per USP ‹621› | ≥ 98.0% area |
| Water content (Karl Fischer) | Metrohm 870 KF Titrino, ASTM E203-16 | ≤ 0.5% w/w |
| Residual solvents | Headspace GC-MS; limits per USP ‹467› Option 1 | Ethyl acetate ≤ 500 ppm, DMF ≤ 880 ppm |
| Heavy metals | ICP-MS; USP ‹233› | Pb ≤ 10 ppm, Cd ≤ 5 ppm, As ≤ 3 ppm, Hg ≤ 1 ppm |
| Storage condition | — | Long-term: -20 ± 5 °C, desiccated, under argon |
Thermal gravimetric analysis (TGA) on a TA Instruments Q500 under nitrogen at 10 °C/min shows no mass loss below 180 °C, indicating a non-solvated crystalline form. Differential scanning calorimetry (DSC, 10 °C/min, crimped Al pan) produces a single sharp endotherm with Tonset between 165 °C and 172 °C, consistent with a single polymorph. Samples stored under the recommended condition of -20 °C in amber glass vials purged with argon retain ≥ 97% HPLC purity after 24 months, as documented in ongoing real-time stability monitoring aligned with ICH Q1A(R2) for non-registered intermediates. Accelerated testing at 40 °C / 75% RH for 6 months shows primary degradation via hydrolysis of the exocyclic carboxamide, generating 3-ethyl-4-methyl-2-oxo-1H-pyrrole and 2-[4-(aminosulfonyl)phenyl]ethanamine as the major degradants; the hydrolysis rate constant at pH 7.4 and 37 °C approximates 1.2 × 10-3 h-1. Accordingly, aqueous stock solutions are acidified to pH 5.0–5.5 and used within 8 hours. Oxidation at the sulfonamide nitrogen has not been detected under ambient light, but exposure to UV-B (280–315 nm) in solution promotes slow sulfonamide N–S cleavage; light-protective packaging is therefore specified.
Compared with widely used 4-sulfamoylphenethylamine intermediates that lack the pyrrolinone cap, BCX-2247 presents the sulfonamide anchor at a fixed distance and angular geometry enforced by the carboxamide-pyrrolinone linkage. This conformationally restricted architecture reduces the number of rotatable bonds from 7 (in a simple flexible conjugate) to 4, an attribute valued in fragment-based lead discovery where rigidified scaffolds often yield improved ligand efficiency. Unsubstituted 2-oxopyrrole-1-carboxamide analogs (i.e., lacking 3-ethyl and 4-methyl groups) show 3- to 5-fold lower microsomal stability in side-by-side intrinsic clearance assays when the heterocycle is not shielded by alkyl substituents; the ethyl/methyl pattern in BCX-2247 furnishes both steric occlusion of the metabolically labile C5 position and a logD adjustment that maintains permeability across Caco-2 monolayers (Papp typically 8–15 × 10-6 cm/s at pH 6.5). Where N-sulfonylurea or N-sulfonylamide derivatives rely on the acidity of the sulfonamide NH, BCX-2247 retains a neutral primary sulfonamide (pKa ~10.3) that avoids confounding salt-bridge requirements and facilitates crystallization and formulation into neutral solid-dispersion matrices. Another differentiating feature concerns manufacturing reproducibility: the synthesis route for BCX-2247 employs a solvent-free melt condensation between 3-ethyl-4-methyl-2-oxo-1H-pyrrole-1-carbonyl chloride and 4-(2-aminoethyl)benzenesulfonamide hydrochloride, followed by aqueous work-up and recrystallization from ethyl acetate/hexanes. This sequence consistently yields product with less than 0.2% of the dimeric impurity that plagues solution-phase carbodiimide-mediated coupling methods—a critical advantage when the compound is used as a key raw material for GLP toxicology batches that require impurity qualification per ICH Q3A.
The compound should be considered incompatible with strong anhydride or chloroformate reagents in the presence of tertiary amine bases, as competitive acylation of the sulfonamide nitrogen leads to N-acylsulfonamide byproducts that co-elute with the parent under typical reversed-phase conditions (ΔtR < 0.3 min). At scales exceeding 100 mmol, the neutralization exotherm during post-synthetic work-up requires jacket cooling to -5 °C to suppress retro-amide cleavage that becomes detectable above 15 °C. Mechanical stirring at 400–600 rpm in a baffled reactor (L/D 1.2:1) is recommended to maintain suspension of the crystalline free base during pH adjustment. In terms of material compatibility, prolonged contact with glass-lined vessels at acidic pH below 2.0 has not caused measurable degradation, but the use of high-nickel alloys (e.g., Hastelloy C-276) should be avoided when handling DMSO stock solutions that may contain traces of chloride, as pitting corrosion liberating Ni2+ can complex with the sulfonamide and impart a green discoloration visible at concentrations as low as 5 ppm.
For accelerated formulation screening, solid dispersions with polyvinylpyrrolidone-vinyl acetate copolymer (Kollidon VA 64) prepared by spray drying from acetone/water (4:1 v/v) have achieved amorphous stabilization with a glass transition temperature (Tg) of 92 °C at 30 wt% drug load, as measured by modulated DSC. The absence of a basic amine in the scaffold simplifies pH-solubility profiling; the intrinsic dissolution rate in FaSSIF media (pH 6.5) at 37 °C and 50 rpm paddle speed is 12 μg·min-1·cm-2, adequate for permeability-limited absorption without requiring salt formation.
