6-Chloropyridine-3-sulfonamide Chemical Properties

Melting point:

158-159 °C(Solv: water (7732-18-5))

Boiling point:

383.2±52.0 °C(Predicted)

Density 

1.558±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

9.24±0.60(Predicted)

6-Chloropyridine-3-sulfonamide Usage And Synthesis

Uses

6-Chloro-3-pyridinesulfonamide, is a heterocylic building block used for chemical synthesis. It can also be used for the synthesis of diuretics and carbonic anhydrase inhibitors.

Synthesis

The general procedure for the synthesis of 6-chloro-3-sulfapyridine from 2-chloropyridine-5-sulfonyl chloride was as follows: 6-chloropyridine-3-sulfonyl chloride (5.0 g, 0.024 mol) was dissolved in a 0.5 M ammonia dioxane solution (125 mL) at -50 °C. The reaction mixture was slowly warmed to room temperature and stirred continuously for 1 hour. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filter cake was washed twice with dioxane. The filtrate was concentrated in vacuum to afford 6-chloropyridine-3-sulfonic acid amide as an off-white solid in a yield of 4.55 g (98% yield). The product was analyzed by liquid chromatography (LC) under the detection condition of UV215 nm; retention time (Rt) 1.05 min and 100% purity. Mass spectrometry (m/z) analytical result (ES+): 193/195. NMR hydrogen spectroscopy (400 MHz; d6-DMSO) data: δ 8.79 (1H, d), 8.21 (1H, dd), 7.75 (1H, d), 7.70 (2H, br s).

References

[1] Patent: WO2008/49605, 2008, A1. Location in patent: Page/Page column 15-16
[2] Patent: WO2008/138594, 2008, A1. Location in patent: Page/Page column 16
[3] Patent: WO2008/21389, 2008, A2. Location in patent: Page/Page column 253
[4] Patent: WO2007/44729, 2007, A2. Location in patent: Page/Page column 186
[5] Patent: WO2008/127594, 2008, A2. Location in patent: Page/Page column 376

6-Chloropyridine-3-sulfonamide(40741-46-6)Related Product Information

• Sulfachoropyrazine sodium
• Sulfanilamide
• Sulfasalazine
• Pentachloropyridine
• Clopidol
• 2-Chloro-3-cyanopyridine
• Sulfapyridine
• Sulfachloropyridazine sodium
• 4-CHLOROPYRIDINE-3-SULFONAMIDE 4-CHLORO-PYRIDINE-3-SULFONIC ACID AMIDE,4-CHLOROPYRIDINE-3-SULFONAMIDE
• 3-Pyridinesulfonamide
• 6-Chloropyridine-3-sulfonamide
• 6-chloro-N-pentylpyridine-3-sulfonamide
• 6-chloro-N-(2-methylphenyl)pyridine-3-sulfonamide
• 6-chloro-N-(3-methylphenyl)pyridine-3-sulfonamide
• 6-chloro-N,N-dipropylpyridine-3-sulfonamide
• 6-chloro-N,N-dimethylpyridine-3-sulfonamide
• 6-chloro-N-(4-chlorophenyl)pyridine-3-sulfonamide
• N-(4-bromophenyl)-6-chloropyridine-3-sulfonamide