[ CAS No. 53250-82-1 ]

Name: 53250-82-1|4-(Methylsulfonamido)aniline|95%
Brand: Ambeed
SKU: A551601
Price: 16.0 USD
Availability: InStock
Rating: 92 (40 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 53250-82-1 * Storage: {[proInfo.prStorage]}

Cart0 Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 88K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 53250-82-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 53250-82-1 ]

SDS

Alternatived Products of [ 53250-82-1 ]

Product Details of [ 53250-82-1 ]

CAS No. :	53250-82-1	MDL No. :	MFCD00463916
Formula :	C₇H₁₀N₂O₂S	Boiling Point :	362.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	186.23 g/mol	Pubchem ID :	3732577
Synonyms :

Safety of [ 53250-82-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 53250-82-1 ]

Upstream synthesis route of [ 53250-82-1 ]
Downstream synthetic route of [ 53250-82-1 ]

[ 53250-82-1 ] Synthesis Path-Upstream 1~1

1
[ 96-67-3 ]
[ 53250-82-1 ]
[ 108-46-3 ]
[ 96-75-3 ]

Reference： [1] Patent: US4491543, 1985, A,

[ 53250-82-1 ] Synthesis Path-Downstream 1~26

1
[ 5825-62-7 ]
[ 53250-82-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; at 25℃; under 760.051 Torr; for 96h;	5% Palladium on carbon ("wet", 11.1 g) was added to a solution of N-(4-nitro- phenyl)-methanesulfonamide (111.4 g, 0.52 mol) in tetrahydrofuran (900 mL) at 25 0C. The atmosphere above the resulting suspension was replaced with hydrogen gas and the reaction mixture was maintained under 1 atmosphere of hydrogen at 25 0C for 4 days using several balloons. The mixture was then filtered through Celite and the Celite was washed with tetrahydrofuran (3 x 100 mL). The combined filtrate and washings were concentrated in vacuo to approximately 300 mL volume and heptane (500 mL) was added dropwise via addition funnel over 45 min at 25 0C with vigorous stirring. The resulting suspension was stirred for an additional 45 min at 25 0C, and then was filtered through medium paper using a Buchner funnel. The collected solid was washed with heptane (1 x 150 mL) and was air-dried to afford the desired product, N-(4-amino-phenyl)-methanesulfonamide (90.7 g, 0.49 mol, 95%) as a beige powder. 1H nuMR (400 MHz, OMSO-d6) delta 2.79 (3H, s), 5.00 (2H, s), 6.49 (2H, d, / = 8.5 Hz), 6.87 (2H, d, / = 8.6 Hz), 8.87 (IH, s).
95%	With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; at 25℃; under 760.051 Torr; for 96h;Product distribution / selectivity;	5% Palladium on carbon ("wet", 11.1 g) was added to a solution of N-(4-nitro- phenyl)-methanesulfonamide (Example 3a', 111.4 g, 0.52 mol) in tetrahydrofuran (900 mL) at 25 0C. The atmosphere above the resulting suspension was replaced with hydrogen gas and the reaction mixture was maintained under 1 atmosphere of hydrogen at 25 0C for 4 days using several balloons. The mixture was then filtered through Celite and the Celite was washed with tetrahydrofuran (3 x 100 mL). The combined filtrate and washings were concentrated in vacuo to approximately 300 mL volume and heptane (500 mL) was added dropwise via addition funnel over 45 min at 25 0C with vigorous stirring. The resulting suspension was stirred for an additional 45 min at 25 0C, and then was filtered through medium paper using a Buchner funnel. The collected solid was washed with heptane (1 x 150 mL) and was air-dried to afford the desired product, N-(4-amino-phenyl)-methanesulfonamide (90.7 g, 0.49 mol, 95% yield) as a beige powder. 1H nuMR (400 MHz, DMSO-^) delta 2.79 (3 H, s), 5.00 (2H, s), 6.49 (2H, d, J= 8.5 Hz), 6.87 (2H, d, J= 8.6 Hz), 8.87 (IH, s).
71%	With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; N,N-dimethyl-formamide; at 20 - 50℃; for 4.5h;	[0364] N-(4-Amino-phenylVmethanesulfonamide (83a).; N-(4-Nitro-phenyl)-methanesulfonamide (82a) (25 g, 115.62 mmol) was dissolved in N,N-dimethylformamide (15 mL) with gentle heating to ~500C via heat gun. Ethyl acetate (100 mL) and methyl alcohol (100 mL) were added followed by 10% palladium on carbon (4 g). The mixture was degassed while stirring and the flask was charged with hydrogen gas via balloon. The mixture stirred at room temperature for 4.5 hours. The mixture was filtered through celite (rinsed with ethyl acetate) and concentrated in vacuo to a yellow green solution with a volume of ~10 mL. Methylene chloride (-50 mL) was added and a solid began to precipitate. The mixture stirred at room temperature for 30 minutes. The solid was collected by vacuum filtration and dried in vacuo to afford the desired product, N-(4-amino- phenyl)-methanesulfonamide 83a (15.32 g, 71 % yield) as a beige powder. 1HNMR (400 MHz, DMSO-d6) delta: 2.79 (s, 3H), 5.00 (s, 2H), 6.49 (d, 2H, J= 8.5 Hz), 6.87 (d, 2H, J= 8.6 Hz), 8.87 (s, IH).

71%	With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; N,N-dimethyl-formamide; at 25 - 50℃; for 4.5h;Product distribution / selectivity;	N-(4-Nitro-phenyl)-methanesulfonamide (Example 3a, 25 g, 115.62 mmol) was dissolved in N,N-dimethylformamide (15 mL) with gentle heating to -50 0C via heat gun. Ethyl acetate (100 mL) and methanol (100 mL) were added followed by 10% palladium on carbon (4 g). The mixture was degassed while stirring and the flask was charged with hydrogen gas via balloon. The mixture was stirred at 25 0C for 4.5 h. The mixture was filtered through Celite (rinsed with ethyl acetate) and concentrated in vacuo to a yellow green solution with a volume of -10 mL. Dichloro methane (-50 mL) was added and a solid began to precipitate. The mixture was stirred at 25 0C for 30 min. The solid was collected by vacuum filtration and dried in vacuo to afford the desired product, N-(4-amino-phenyl)-methanesulfonamide (15.32 g, 82.26 mmol, 71 % yield) as a beige powder. 1H nuMR (400 MHz, DMSO- d6) delta 2.79 (3H, s), 5.00 (2H, s), 6.49 (2H, d, J= 8.5 Hz), 6.87 (2H, d, J= 8.6 Hz), 8.87 (IH, s).
71%	With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; N,N-dimethyl-formamide; at 25℃; for 4.5h;	N-(4-Aminophenyl)methanesulfonamide N-(4-nitrophenyl)methanesulfonamide (25 g, 115.62 mmol) was dissolved in N,N-dimethylformamide (15 mL) with gentle heating to ~50 C. via heat gun. Ethyl acetate (100 mL) and methanol (100 mL) were added followed by 10% palladium on carbon (4 g). The mixture was degassed while stirring and the flask was charged with hydrogen gas via balloon. The mixture stirred at 25 C. for 4.5 hours. The mixture was filtered through celite (rinsed with ethyl acetate) and concentrated in vacuo to a yellow green solution with a volume of ~10 mL. Dichloromethane (~50 mL) was added and a solid began to precipitate. The mixture stirred at 25 C. for 30 minutes. The solid was collected by vacuum filtration and dried in vacuo to afford the desired product, N-(4-aminophenyl)methanesulfonamide (15.32 g, 82.26 mmol, 71% yield) as a beige powder 1H NMR (400 MHz, DMSO-d6) delta 2.79 (3H, s), 5.00 (2H, s), 6.49 (2H, d, J=8.5 Hz), 6.87 (2H, d, J=8.6 Hz), 8.87 (1H, s).
67%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h;	To a solution of intermediate compound 8 (3.23 mmol, 0.70 g) in MeOH (7 ml_) Pd/C 10 % (10% w/w, 70 mg) was added and the mixture was hydrogenated at room temperature for 16 hours. After that, the reaction mixture was filtered through a pad of Celite washing with THF. The solvent was evaporated under vacuum to give the title compound which was used at the next step without further purification. (0.4 g. Yield= 67%) 1 H NMR (400 MHz, DMSO-d6) delta 8.95 (1 H, brs), 6.94 (2H, d, J = 8.8 Hz), 6.56 (2H, d, J = 8.8 Hz), 5.06 (1 H, brs), 2.85 (3H, s). LC-MS: tR =0.36 [M+H]+= 187 (method 3)
49%	With palladium 10% on activated carbon; ammonium formate; In methanol; at 45℃;Inert atmosphere; Cooling with ice;	To a solution of N-(4-nitrophenyl)methanesulfonamide (23.0 g, 106.48 mmol) in MeOH (100 mL) was added 10% Pd/C (3.0 g) purged with N2. Then a solution of HCO2NH4 (67.0 g, 1.06 mol) in MeOH (500 mL) was added gradually under ice-water bath during 5 min. After addition, the mixture was warmed to 45 C, stirred overnight, and then filtered. The filtrate was evaporated under reduced pressure to afford yellow solid which was washed with EA (500 mL x 3). The combined organic layers were evaporated under reduced pressure, purified by silica gel column chromatography (PE:EA = 1:2) to afford N-(4-aminophenyl)methanesulfonamide as a yellow solid (9.80 g, yield 49%).
49%	With palladium 10% on activated carbon; ammonium formate; In methanol; at 45℃;Inert atmosphere; Cooling with ice;	Compound 23-3, R?H (0438) To a solution of 23-2, R?H (23.0 g, 106.48 mmol) in MeOH (100 mL) was added 10% Pd/C (3.0 g) purged with N2. Then a solution of HCO2NH4 (67.0 g, 1.06 mol) in MeOH (500 mL) was added gradually under ice-water bath during 5 min. After addition, the mixture was warmed to 45 C. and stirred overnight and filtered. The filtrate was evaporated under reduced pressure to afford yellow solid which was washed with EA (500 mL×3). The combined organic layers were evaporated under reduced pressure, purified by silica gel column chromatography (PE:EA=1:2) to afford N-(4-aminophenyl)methanesulfonamide as a yellow solid (9.80 g, yield 49%).
	With iron; ammonium chloride; In ethanol; water; for 2h;Reflux;	[0007901 To a stirred solution of compoundS (0.8 g, 1 eq) in ethanol (20 mL), iron powder (1.03 g, 5 eq), water (20 mL) and ammonium chloride (0.98 g,5 eq) were added slowly. The reaction mixture was heated to reflux for 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and evaporated under reduced pressure. The residue was dissolved in ethyl acetate (50 mL) and washed with brine. The organic extract was dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford the title compound 6.?H NMR (400 MHz, DMSO-d6) oe:8.89 (s, 1H), 6.88 (d, J= 8.0 Hz, 2H), 6.50(d, J= 8.8 Hz, 2H), 5.01 (s, 2H), 2.79(s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4136 - 4142
[2]Synthetic Communications,2008,vol. 38,p. 1909 - 1916
[3]Patent: WO2008/73982,2008,A2 .Location in patent: Page/Page column 66
[4]Patent: WO2007/150001,2007,A1 .Location in patent: Page/Page column 48; 70
[5]Journal of Medicinal Chemistry,2016,vol. 59,p. 7212 - 7222
[6]Patent: WO2008/82725,2008,A1 .Location in patent: Page/Page column 168-169
[7]Patent: WO2007/150001,2007,A1 .Location in patent: Page/Page column 48; 68
[8]Patent: US2008/188466,2008,A1 .Location in patent: Page/Page column 24
[9]Patent: WO2013/149997,2013,A1 .Location in patent: Page/Page column 45
[10]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2338 - 2342
[11]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 299-300
[12]Journal of the Chemical Society,1910,vol. 97,p. 58
[13]Tetrahedron,1986,vol. 42,p. 5739 - 5746
[14]Heterocycles,1992,vol. 34,p. 2301 - 2311
[15]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3411 - 3420
[16]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5647 - 5647
[17]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000790
[18]Patent: US2663732,1950,
[19]ChemMedChem,2019,vol. 14,p. 1514 - 1527

2
[ 66074-67-7 ]
[ 53250-82-1 ]
[ 137265-19-1 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1991,vol. 30,p. 853 - 858

3
[ 1189-71-5 ]
[ 53250-82-1 ]
C₈H₁₀ClN₃O₅S₂ [ No CAS ]