N-(4-Acetyl-phenyl)-methanesulfon-amide

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N-(4-Acetyl-phenyl)-methanesulfon-amide Basic information
Product Name:N-(4-Acetyl-phenyl)-methanesulfon-amide
Synonyms:AURORA 2940;N-(4-ethanoylphenyl)methanesulfonamide;N-(4-Acetylphenyl);Methanesulfonamide, N-(4-acetylphenyl)-;4'-Acetylmethanesulfonanilide;4'-ACETYLMETHANESULFONANILIDE;N-(4-Acetyl-phenyl)-methanesulfon-amide
CAS:5317-89-5
MF:C9H11NO3S
MW:213.25
EINECS:
Product Categories:
Mol File:5317-89-5.mol
N-(4-Acetyl-phenyl)-methanesulfon-amide Structure
N-(4-Acetyl-phenyl)-methanesulfon-amide Chemical Properties
Melting point 150-152 °C
Boiling point 369.4±44.0 °C(Predicted)
density 1.320±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka7.16±0.10(Predicted)
AppearanceWhite to light yellow Solid
Safety Information
Hazard Codes Xi
HazardClass IRRITANT
MSDS Information
N-(4-Acetyl-phenyl)-methanesulfon-amide Usage And Synthesis
Synthesis
4-Aminoacetophenone

99-92-3

Methanesulfonyl chloride

124-63-0

N-(4-ACETYL-PHENYL)-METHANESULFON-AMIDE

5317-89-5

Cooled 4-aminoacetophenone (10 mmol) was dissolved in pyridine (10 mL) at 0 °C and methanesulfonyl chloride (15 mmol) was added slowly. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was diluted with H2O and extracted with ethyl acetate (EtOAc) several times. The organic layers were combined, washed sequentially with H2O and saturated brine and dried over anhydrous magnesium sulfate (MgSO4). After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by rapid column chromatography on silica gel, the eluent being a mixed solvent of ethyl acetate:hexane to afford N-(4-acetylphenyl)methanesulfonamide (Compound 13-5, LJO-298). The yield was 95% and the melting point was 161 °C. 1H NMR (CDCl3) δ: 7.97 (dd, 2H, J = 2.0, 6.8 Hz), 7.26 (dd, 2H, J = 2.0, 6.8 Hz), 6.87 (bs, 1H), 3.10 (s, 3H), 2.59 (s, 3H).

References[1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 6, p. 846 - 867
[2] Organic Process Research and Development, 1998, vol. 2, # 2, p. 71 - 77
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 18, p. 6043 - 6053
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2685 - 2688
[5] Patent: WO2005/3084, 2005, A1. Location in patent: Page 79
N-(4-Acetyl-phenyl)-methanesulfon-amide Preparation Products And Raw materials
Raw materials4-Aminoacetophenone-->Methanesulfonyl chloride
Preparation ProductsN-[4-(2-Bromoacetyl)phenyl]methanesulfonamide
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