4-Chloro-3-pyridinesulfonamide
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4-Chloro-3-pyridinesulfonamide
structure -
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CAS No:
33263-43-3
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Formula:
C5H5ClN2O2S
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Chemical Name:
4-Chloro-3-pyridinesulfonamide
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Synonyms:
3-Pyridinesulfonamide,4-chloro-;4-Chloro-3-pyridinesulfonamide;4-Chloro-3-pyridylsulfonamide
- Categories:
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CAS No:
4-Chloro-3-pyridinesulfonamide Basic Attributes
192.62
192.62
251-434-4
QY6G99E6Q2
DTXSID50186904
2935009090
Characteristics
81.4
0
off-white to light beige powder
1.6±0.1 g/cm3
155-157 °C @ Solvent: Water
380.4°C at 760 mmHg
183.9±30.7 °C
1.592
soluble
Safety Information
III
2811
R22;R36/37/38
S36/37
Xn:Harmful;
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H302 (13.04%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-Chloro-3-pyridinesulfonamide Use and Manufacturing
A mixture of A solution of To a 100 mL RBF was added 4-chloro-3- pyridinesulfonamide (commercially available from Alfa Aesar, 0.56 g, 2.91 mmol) in AcOH (25 mL). N2 was bubbled through the suspension for 5 mm before platinum (IV) oxide (commercially available from Sigma-Aldrich, USA, 0.330 g, 1.45 mmol) was added under N2 flow. The flask was then sealed with a septum and placed under vacuum. Hydrogen gas was back-filled from a balloon. The reaction mixture was stirred at RT under hydrogen gas for 3 days. Celite® brand filter aid (20 g) was added to the stirred mixture. The solution was then filtered through a short pad of Celite® brand filter aid. The pad was rinsed with MeOH. The combined organic layers were concentrated in vacuo to give a light-yellow glass. The residue was triturated with DCM to afford Example 179.1 (0.6 g, 2.99 mmol, 103 percent yield) as a light yellow solid. LCMS-ESI (pos.), m/z: 165.2 (M+H)t[03221 (S)-Piperidine-3-sulfonamide hydrochloride and (R)-piperidine-3- sulfonamide hydrochloride, Example 38.1. A solution of 4-chloropyridine-3- sulfonamide (5.0 g, 25.9 mmol) in AcOH (150 mL) was placed in a Parr bottle. The solution was bubbled with nitrogen gas for 5 mm. To this solution was added a suspension of platinum (IV) oxide (5.9 g, 25.9 mmol) in AcOH (30 mL). The reaction was stirred under an atmosphere of hydrogen (50 psi) for 72 h. The reaction mixture was then filtered through a Celite® brand filter aid pad, and the pad was washed with MeOH (2 x 50 mL). The combined filtrate was concentrated under reduced pressure to provide initial Example 38.1 (6.0 g) as oil which was used in the next step without further purification. LCMS-ESI (pos.) m/z: 165 (M+H)t(3R, 5R)-1-(5-Fluoropyrimidin-2-yl)-5-isopropoxypiperidine-3-sulfonamide or (3S, 5S)-1-(5-fluoropyrimidin-2-yl)-5-isopropoxypiperidine-3-sulfonamide, Example 179.8 Further elution under the conditions described in Example 179.5 gave Example 179.8 as the fourth peak. 1H NMR (400 MHz, CD3OD) delta 0.92 (d, J=6.12 Hz, 3H) 1.08 (d, J=6.01 Hz, 3H) 1.98 (ddd, J=13.19, 12.15, 2.95 Hz, 1H) 2.33 (dtdd, J=13.26, 3.68, 3.68, 1.97, 1.87 Hz, 1H) 3.01 (dd, J=14.10, 1.66 Hz, 1H) 3.13 (dd, J=13.06, 10.99 Hz, 1H) 3.33-3.45 (m, 1H) 3.74 (dt, J=12.13, 6.06 Hz, 1H) 3.86-3.93 (m, 1H) 4.77-4.83 (m, 1H) 5.11 (ddt, J=13.05, 3.69, 1.79, 1.79 Hz, 1H) 8.27 (d, J=0.62 Hz, 2H). LCMS-ESI (pos) m/z: 319.2 (M+H)+.To a 100 mL RBF was added To a 100-mL round-bottomed flask was added A solution of 4-chloropyridine-3- sulfonamide (5.0 g, 25.9 mmol) in AcOH (150 mL) was placed in a parr bottle. The mixture was bubbled with nitrogen gas for 5 min. To this solution was added a suspension of platinum (IV) oxide (5.9 g, 25.9 mmol) in AcOH (30 mL). The reaction was stirred under an atmosphere of hydrogen (50 psi) for 72 h. The reaction mixture was filtered through Celite® brand filter agent pad and the pad was washed with MeOH (2 x 50 mL). The combined filtrate was concentrated under reduced pressure to provide Example 92.1 (6.0 g) as an oil which was used in the next step without further purification. LCMS-ESI (pos.) m/z: 165.2 (M+H)+.
Computed Properties
Molecular Weight:192.62
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:191.9760263
Monoisotopic Mass:191.9760263
Topological Polar Surface Area:81.4
Heavy Atom Count:11
Complexity:223
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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