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[ CAS No. 55512-05-5 ] {[proInfo.proName]}

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Chemical Structure| 55512-05-5
Chemical Structure| 55512-05-5
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Product Details of [ 55512-05-5 ]

CAS No. :55512-05-5 MDL No. :MFCD03198179
Formula : C8H9NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :CBDSSTWZEANOCR-UHFFFAOYSA-N
M.W : 199.23 Pubchem ID :2794787
Synonyms :

Safety of [ 55512-05-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55512-05-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 55512-05-5 ]

[ 55512-05-5 ] Synthesis Path-Downstream   1~33

  • 1
  • [ 124-63-0 ]
  • [ 1709-44-0 ]
  • [ 55512-05-5 ]
YieldReaction ConditionsOperation in experiment
42% With pyridine; In dichloromethane; at 20℃; 1.3 g (10.73 mmol) of 3-aminobenzenecarbaldehyde were initially charged in 30 ml of dichloromethane. 849 mg (10.73 mmol) of pyridine and 1.3 g (10.73 mmol) of methanesulfonyl chloride were added, and the mixture was then stirred at RT overnight. Ethyl acetate was added, and the reaction solution was washed in each case once with 1 N hydrochloric acid, water and saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel 60 (mobile phase: dichloromethane/methanol 100/0?50/1). Yield: 935 mg (42% of theory) LC-MS (Method 8): Rt=1.20 min; MS (ESIpos): m/z=198 [M-H]-.
YieldReaction ConditionsOperation in experiment
Preparation 1 m-(Methylsulfonamido)Benzaldehyde m-(Amino)benzaldehyde polymer (1210 g, 10.0 mole), THF (12,000 ml), and water (495 ml) were combined and stirred overnight at room temperature. The resultant slurry was cooled to between about 5 to about 10C and pyridine (1580 g, 20 moles) was added. Methylsulfonyl chloride (2290 g, 20 moles) was added in a dropwise fashion to the slurry while maintaining the temperature of reaction solution at approximately 10C. The reaction was stirred in an ice bath overnight, during which time the ice in the bath melted and the temperature of the reaction climbed to between about 15 to 20C. The THF was removed in vacuo and 1N hydrochlor ic acid (6 l) was added to the residue. The resultant slurry was stirred at room temperature for approximately 8 hours. The orange, granular material of the slurry was collected on a filter, was washed with water (approximately 6 liters) and was dried for 48 hours at 40C to yield 1833 g of material. A portion of this material (940 g) was recrystallized from an ethyl acetate mixture containing carbon black and sodium carbonate. Two crops of crystals from this solution yielded 874 g of m-(methylsulfonamido)benzaldehyde: n.m.r. (360 MHz, DMSO-d6): delta 3.05 (s,3), 7.5-7.9 (m, 4), 9.9 (s,1), 10.1 (s,1).
Preparation 1 m-(Methylsulfonylamino)benzaldehyde m-(Amino)benzaldehyde polymer (1210 g, 10.0 mole), THF (12,000 ml), and water (495 ml) were combined and stirred overnight at room temperature. The resultant slurry was cooled to between about 5 to about 10C and pyridine (1580 g, 20 moles) was added. Methylsulfonyl chloride (2290 g, 20 moles) was added in a dropwise fashion to the slurry while maintaining the temperature of reaction solution at approximately 10C. The reaction was stirred in an ice bath overnight, during which time the ice in the bath melted and the temperature of the reaction climbed to between about 15 to 20C. The THF was removed in vacuo and 1N hydrochloric acid (6 l) was added to the residue. The resultant slurry was stirred at room temperature for approximately 8 hours. The orange, granular material of the slurry was collected on a filter, was washed with water (approximately 6 liters) and was dried for 48 hours at 40C to yield 1833 g of material. A portion of this material (940 g) was recrystallized from an ethyl acetate mixture containing carbon black and sodium carbonate. Two crops of crystals from this solution yielded 874 g of m-(methylsulfonylamino)benzaldehyde: n.m.r. (360 MHz, DMSO-d6): delta 3.05 (s,3), 7.5-7.9 (m, 4), 9.9 (s,1), 10.1 (s,1).
  • 3
  • [ 75-52-5 ]
  • [ 55512-05-5 ]
  • <i>N</i>-[3-(1-hydroxy-2-nitro-ethyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 4
  • [ 16642-79-8 ]
  • [ 55512-05-5 ]
  • 3-[4-(3-methanesulfonylamino-benzylamino)-phenyl]-propionic acid [ No CAS ]
  • 5
  • [ 55512-05-5 ]
  • <i>N</i>-[3-(2-amino-1-triethylsilanyloxy-ethyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 6
  • [ 55512-05-5 ]
  • <i>N</i>-[3-(2-nitro-1-triethylsilanyloxy-ethyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 7
  • [ 55512-05-5 ]
  • (+/-)-N-(3-{1-hydroxy-2-[3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-2-oxo-1,2-dihydro-pyridin-4-ylamino]-ethyl}-phenyl)-methanesulfonamide [ No CAS ]
  • 9
  • [ 55512-05-5 ]
  • [ 107-19-7 ]
  • C10H11NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In benzene;Heating / reflux; To a 300 ml solution of 29.79 g (95.4 MMOL) of compound 4 in benzene are added 80 ml of triethylamine, 0.671 g (0.956 MMOL) of palladium bistriphenylenephosphine dichloride, 0.091 g (0.478 MMOL) of copper iodide and 16.7 ml (287 MMOL) or propargyl alcohol and the mixture is heated to reflux overnight. The reaction mixture is concentrated under reduced pressure. The residue is combined with ether and filtered to remove insoluble materials. Purification by chromatography on silica gel gives 5.19 g (18.1 mmol ; yield, 19%) of the objective compound 5 as an oil. Although it contains a little solvent, it is used in the next reaction as it is.
  • 10
  • [ 376347-09-0 ]
  • [ 55512-05-5 ]
YieldReaction ConditionsOperation in experiment
97% With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1h; C. 3-[(MethyIsulfonyl)amino]benzaldehyde.; [3-(Hydroxymethyl) phenyl](methylsulfonyl) amine (0.42 g, 2.08 mmol) was dissolved in dichloromethane (20 mL) followed by addition of pyridinium chlorochromate (0.67 g, 3.12 mmol). The reaction was stirred at rt for IH. Filtered crude reaction through a plug of silica gel and washed with 60% EtOAc/Hex (250 mL), removed volatiles under reduced pressure to afford the title compound (0.40 g, 2.01 mmol, 97%) as a white solid. MS (ESI) m/z 200.2 [M+l]+ [00391]
94% With pyridinium chlorochromate; In dichloromethane; at 20℃; for 1.16667h;Molecular sieve; To a 1500 ml solution of 22.06 g (83.8 MMOL) of compound 3 in methylene chloride are added 44 g of molecular sieve 4A (powder) and 32.5 g (151 MMOL) of pyridinium chlorochromate and the mixture is stirred fro 70 min at room temperature. The reaction mixture is purified by column chromatography on silica gel eluting with methylene chloride to yield 20.46 g (78.3 mmol ; yield, 94% of compound 4
  • 11
  • [ 1336-21-6 ]
  • [ 55512-05-5 ]
  • [ 55512-06-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; ammonium chloride; Preparation 2 D,L-2-(Amino)-2-(m-(Methylsulfonamido)phenyl)acetonitrile Concentrated ammonium hydroxide (43 ml) was cooled to 10C. Sodium cyanide (5.4 g, 110 mmol), ammonium chloride (5.5 g, 102 mmol), and <strong>[55512-05-5]m-(methylsulfonamido)benzaldehyde</strong> (10.0 g, 50 mmol) were added and the resultant solution was stirred for 4 hours between about 10 to 15C. Excess ammonia of the solution was removed in vacuo at 15C. The pH of the residue was adjusted to 7.0 by the addition of concentrated hydrochloric acid. The resultant solution was extracted with ethyl acetate (6X) and the ethyl acetate extractions were combined, washed with brine (2X), dried over magnesium sulfate, filtered, and evaporated in vacuo to yield 10.6 g, 94 % of a brown oil of D,L-2-(amino)-2-((m-methylsulfonamido)phenyl)acetonitrile: n.m.r. (DMSO-d6, 90 MHz): delta 3.0 (s,3), 5.0 (s,1), 7.2-7.6 (m, 4).
With hydrogenchloride; ammonium chloride; Preparation 2 D,L-2-(amino)-2-(m-(methylsulfonylamino)phenyl)acetonitrile Concentrated ammonium hydroxide (43 ml) was cooled to 10C. Sodium cyanide (5.4 g, 110 mmol), ammonium chloride (5.5 g, 102 mmol), and <strong>[55512-05-5]m-(methylsulfonylamino)benzaldehyde</strong> (10.0 g, 50 mmol) were added and the resultant solution was stirred for 4 hours between about 10 to 15C. Excess ammonia of the solution was removed in vacuo at 15C. The pH of the residue was adjusted to 7.0 by the addition of concentrated hydrochloric acid. The resultant solution was extracted with ethyl acetate (6X) and the ethyl acetate extractions were combined, washed with brine (2X), dried over magnesium sulfate, filtered, and evaporated in vacuo to yield 10.6 g, 94% of a brown oil of D,L-2-(amino)-2-((m-methylsulfonylamino)phenyl)acetonitrile: n.m.r. (DMSO-d6, 90 MHz): delta 3.0 (s,3), 5.0 (s,1), 7.2-7.6 (m, 4).
  • 12
  • [ 6624-83-5 ]
  • [ 55512-05-5 ]
  • [ 55579-76-5 ]
  • 7-benzo[1,3]dioxol-5-yl-4-(3-methanesulfonylamino-phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid cyclopentyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With ammonium acetate; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 90℃; for 0.166667h; Example 84[0322] Preparation of 7-Benzo[l,3]dioxol-5-yl-4-(3-methanesulfonylamino-phenyl)-2- methyl-5-oxo-l,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid cyclopentyl ester. <n="122"/>[0323] Synthesis of 7-Benzo[l,3]dioxol-5-yl-4-(3-methanesulfonylamino-phenyl)-2- methyl-5-oxo-l,4,5,6,7,8-hexahydro-quinoIine-3-carboxylic acid cyclope?tyl ester (13o):To a small vial was added <strong>[55512-05-5]N-(3-formyl-phenyl)-methanesulfonamide</strong> (86 nig, 0.43 mmol) followed by 5-benzo[l,3]dioxol-5-yl-cyclohexane-l,3-dione (100 mg, 0.43 mmol), ammonium acetate (50 mg, 0.65 mmol), 3-oxo-butyric acid cyclopentyl ester (73 mg, 0.43 mmol) and l-butyl-3-methylimidazolium tetrafluoroborate (9.7 muL, 0.052 mmol). The reaction mixture was then heated at 900C for 10 minutes, cooled down to room temperature, and then loaded on column (50% ethyl acetate/hexanes) to get the desired product (121 mg, 50%) as a yellow solid. MS (ES) M+H expected = 565.2, found = 565.3.
  • 13
  • [ 916059-46-6 ]
  • [ 55512-05-5 ]
  • 14
  • [ 55512-05-5 ]
  • [ 33398-36-6 ]
  • [ 916059-55-7 ]
  • [ 916059-56-8 ]
  • 15
  • [ 55512-05-5 ]
  • [ 68-11-1 ]
  • [ 101-79-1 ]
  • [ 1059198-63-8 ]
YieldReaction ConditionsOperation in experiment
In toluene; at 110℃; for 15h;Heating / reflux; A solution of 4-(4-chlorophenoxy)benzenamine (220 mg, 1.0 mmol) and mercaptoacetic acid (140 muL, 2 mmol) in 3mL of toluene is added 3- (mesylamino)benzaldehyde (262 mg, 1.0 mmol). The resulting solution is stirred and heated at 110 0C for 15 h. The reaction mixture is cooled down to room temperature and concentrated. The residue is purified on silica gel (0-30percent ethyl acetate in hexane) to yield 3-[4-(4-chlorophenoxy)phenyl]-2-(3-mesylaminophenyl)thiazolidin-4-one as a white foam. 1H NMR (CDCl3) delta (ppm) 7.31-7.23 (m, 3H), 7.22-7.14 (m, 2H), 7.13-7.08 (m, 4H), 6.89-6.82 (m, 4H), 6.02 (d, J=1.2 Hz, IH), 4.00 (dd, J=16.0, 1.6 Hz, IH), 3.88 (d, J=15.6 Hz, IH), 2.90 (s, 3H). HPLC-MS calculated C22H19ClN2O4S2 (M+H+) 475.05, found 475.00.
  • 16
  • [ 1821-47-2 ]
  • [ 55512-05-5 ]
  • C19H21N3O2S [ No CAS ]
  • 17
  • [ 55512-05-5 ]
  • [ 1353657-62-1 ]
  • 18
  • [ 55512-05-5 ]
  • [ 75-16-1 ]
  • [ 943410-74-0 ]
YieldReaction ConditionsOperation in experiment
89% Under argon and at 0 C., 83 mg (0.417 mmol) of <strong>[55512-05-5]N-(3-formylphenyl)methanesulfonamide</strong> (Example 86A) were initially charged in 1 ml of abs. tetrahydrofuran. At 0 C., 99 mg (0.833 mmol) of methylmagesium bromide (3 M in diethyl ether) were added dropwise (resulting in the formulation of a precipitate), and the reaction solution was stirred at this temperature for 2 h. The reaction solution was quenched with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Yield: 80 mg (89% of theory) LC-MS (Method 8): Rt=1.15 min; MS (ESIpos): m/z=214 [M-H]-.
  • 19
  • [ 4518-10-9 ]
  • [ 55512-05-5 ]
  • 20
  • [ 32087-05-1 ]
  • [ 55512-05-5 ]
  • 21
  • [ 56341-37-8 ]
  • [ 55512-05-5 ]
  • (E)-3N-[3-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 22
  • [ 17630-75-0 ]
  • [ 55512-05-5 ]
  • (E)-3N-[3-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenyl]-methane sulfonamide [ No CAS ]
  • 23
  • [ 56341-39-0 ]
  • [ 55512-05-5 ]
  • (E)-3N-[3-(6-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenyl]-methane-sulfonamide [ No CAS ]
  • 24
  • [ 56341-41-4 ]
  • [ 55512-05-5 ]
  • (E)-3N-[3-(5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenyl]-methane-sulfonamide [ No CAS ]
  • 25
  • [ 55512-05-5 ]
  • 4,5-difluoro-2-oxindole [ No CAS ]
  • C16H12F2N2O3S [ No CAS ]
  • 26
  • [ 55512-05-5 ]
  • [ 74-88-4 ]
  • N-(3-formylphenyl)-N-methylmethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetone; at 20℃; <strong>[55512-05-5]N-(3-formylphenyl)methanesulfonamide</strong> (465 mg, 2.33 mmol) was dissolved in acetone (10 mL) at room temperature. Powdered K2C03 (968 mg, 7.00 mmol) and iodomethane (0.29 mL, 4.67 mmol) were then added and the reaction mixture allowed to stir overnight. The reaction mixture was poured into water (5 mL) and extracted with EtOAc (3 x 15 mL). The combined organic phases were washed with brine (5 mL),dried over MgSO4 and concentrated to give crude product which was carried on without further purification.
  • 27
  • [ 128-53-0 ]
  • [ 55512-05-5 ]
  • N-(4-(1-ethyl-2,5-dioxopyrrolidin-3-yl)-3-formylphenyl)methanesulfonamide [ No CAS ]
  • 28
  • [ 109-97-7 ]
  • [ 55512-05-5 ]
  • 5,10,15,20-mesotetrakis(3-methylsulfonamidophenyl)-21H,23H-porphyrine [ No CAS ]
  • 29
  • [ 55512-05-5 ]
  • N-(4-chloro-3-formylphenyl)methanesulfonamide [ No CAS ]
  • 30
  • [ 55512-05-5 ]
  • C26H34N6O3 [ No CAS ]
  • C34H43N7O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
26.2 mg Toa solution of <strong>[55512-05-5]3-(methylsulfonamido)benzaldehyde</strong> (31.9mg, 0.16 mmol) and acetic acid (0.018 mL) in methanol (0.4 mL) was added asolution of compound 11a (38.3 mg,0.08 mmol) in tetrahydrofuran (0.2 mL), followed by stirring at roomtemperature under a nitrogen atmosphere. After 15 min, sodium cyanoborohydride(1.0 M in tetrahydrofuran, 0.16 mL, 0.16 mmol) was added to the reactionmixture and the resulting mixture was stirred at room temperature for 1 hour.The mixture was directly subjected to flash column chromatography on silica gel(50:50 to 33:67 hexane/ethyl acetate) to give 26.2 mg of compound 12a.
  • 31
  • [ 55512-05-5 ]
  • C21H23N3O4*C2HF3O2 [ No CAS ]
  • N-(3-[(2S)-2-benzyl-4-[(5-methoxy-1H-indol-2-yl)carbonyl]-6-oxopiperazin-1-yl]methyl}phenyl)methanesulfonamide [ No CAS ]
  • 32
  • [ 55512-05-5 ]
  • N-(3-(cyclopentylmethyl)phenyl)methanesulfonamide [ No CAS ]
  • 33
  • [ 55512-05-5 ]
  • [ 1576-35-8 ]
  • N-(3-((2-tosylhydrazono)methyl)phenyl)methanesulfonamide [ No CAS ]
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