4-(3'-Methylphenyl)amino-3-pyridinesulfonamide
Synonym(s):4-[(3-Methylphenyl)amino]-3-pyridinesulfonamide
- CAS NO.:72811-73-5
- Empirical Formula: C12H13N3O2S
- Molecular Weight: 263.32
- MDL number: MFCD00661332
- EINECS: 615-805-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-06-04 19:18:49
What is 4-(3'-Methylphenyl)amino-3-pyridinesulfonamide?
Chemical properties
White to Off-White Solid
The Uses of 4-(3'-Methylphenyl)amino-3-pyridinesulfonamide
Torasemide intermediate.
What are the applications of Application
4-[(3-Methylphenyl)amino]-3-pyridinesulfonamide is a Torasemide intermediate
Synthesis
4-(3'-Methylphenyl)amino-3-pyridinesulfonamide is prepared by the reaction of 4-Chloropyridine-3-sulfonamide hydrochloride and 3-Methylaniline. The specific synthesis steps are as follows:
EXAMPLE 1; Preparation of 4-(3-methylphenyl)aminopyridine-sulfonamide; 2L three-neck flask, equipped with a mechanical stirrer, thermometer and condenser, was charged with water (500 ml) and 4-chloro-3- pyridinesulfonamide hydrochloride (100g, 0.44 mol). To this suspension was added m-toluidine (49.2 ml, 0.46 mol) at room temperature. The reaction mixture was heated to 90°C for a minimum period of 3 h. The progress of the reaction was followed by HPLC. After completion, the mixture was cooled to room temperature. The pH of the reaction was then adjusted carefully to pH 7-8 with sat. NaHC03 (ca. 1.1 l). The product was precipitated out and isolated by vacuum filtration as beige solid (126.2 g wet weight). The product was then dissolved in MeOH (1.0 l) at room temperature and charged with Darco KB (25g). The solution was refluxed for 0.5 h and then filtered through a patch of celite to remove Darco KB, while still hot, and rinsed with hot MeOH (200 ML). The filtrate was then charged with water (1.2 l) and stirred for a minimum of 1 h at room temperature. The product, which had precipitated out, was isolated by vacuum filtration to obtain a solid 106.3 g (92percent wet weight =>99.8percent purity a/a). 1H NMR (d6-DMSO) ; 2.30 (s, 3H), 7.00-7. 15 (m. 5H), 7.32 (m, 1H), 7.75 (brs, 1.5H), 8.05 (brs, 0.5H), 8.25 (d, 1H), 8.68 (s, 1H).
Properties of 4-(3'-Methylphenyl)amino-3-pyridinesulfonamide
Melting point: | 162-164?C |
Boiling point: | 475.8±55.0 °C(Predicted) |
Density | 1.357±0.06 g/cm3(Predicted) |
storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
solubility | DMSO (Slightly), Methanol (Slightly) |
pka | 9.53±0.60(Predicted) |
form | neat |
color | White to Off-White |
BRN | 5438165 |
CAS DataBase Reference | 72811-73-5(CAS DataBase Reference) |
Safety information for 4-(3'-Methylphenyl)amino-3-pyridinesulfonamide
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 4-(3'-Methylphenyl)amino-3-pyridinesulfonamide
InChIKey | ZXPCUGWAKUIOOF-UHFFFAOYSA-N |
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