[ CAS No. 51803-78-2 ]

Name: 51803-78-2|N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide|98%
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SKU: A370794
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{[proInfo.proName]} (Synonyms:Nimesulide) ,{[proInfo.pro_purity]}

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

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Quality Control of [ 51803-78-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 51803-78-2 ]

SDS Specification

Alternatived Products of [ 51803-78-2 ]

Product Details of [ 51803-78-2 ]

CAS No. :	51803-78-2	MDL No. :	MFCD00079470
Formula :	C₁₃H₁₂N₂O₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HYWYRSMBCFDLJT-UHFFFAOYSA-N
M.W :	308.31	Pubchem ID :	4495
Synonyms :	Nimesulide

Safety of [ 51803-78-2 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P501-P270-P202-P201-P264-P280-P308+P313-P301+P310+P330-P405	UN#:	2811
Hazard Statements:	H301-H361	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 51803-78-2 ]

* 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.

Upstream synthesis route of [ 51803-78-2 ]
Downstream synthetic route of [ 51803-78-2 ]

[ 51803-78-2 ] Synthesis Path-Upstream 1~5

1
[ 51803-78-2 ]
[ 94-13-3 ]
[ 62-44-2 ]
[ 5422-92-4 ]
[ 99-76-3 ]
[ 99-96-7 ]

Reference： [1] Chemical Papers, 2010, vol. 64, # 3, p. 405 - 408

2
[ 5422-92-4 ]
[ 124-63-0 ]
[ 51803-78-2 ]

Yield	Reaction Conditions	Operation in experiment
74.3%	Stage #1: With triethylamine In dichloromethane at 20℃; for 23 h; Cooling with ice Stage #2: With sodium hydroxide In water for 16 h; Reflux	A solution of 4a (500 mg, 2.2 mmol) in anhydrous CH₂Cl₂ (2.2 mL) was treated with dry Et₃N (484 μL, 3.5 mmol) and the mixture was allowed to stir for 1 min at room temperature. To the reaction mixture, CH₃SO₂Cl (840 μL, 10.9 mmol) was added drop-wise at ice-cold temperature. The resulting mixture was stirred for 23 h and the reaction was quenched with distilled water. After extraction with CHCl₃, the combined organic phases were dried and filtered, and the solvent was removed in vacuo. To the residue 3 M NaOHaq (10 mL) was added and the mixture stirred at 80-90 °C for 16 h. Afterwards, 5 M HCl was added and it was extracted with CHCl₃. The combined organic phases were dried and filtered, and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel with CHCl₃/hexane/acetone = 1:8:1 to provide 1a (497.4 mg, 74.3percent) as a pale yellow solid: mp: 142-144 °C (lit ¹⁶ mp: 143-144.5 °C); ¹H NMR (600 MHz, DMSO-d₆) δ ppm: 10.16 (s, 1H), 8.03 (dd, J = 2.7, 9.0 Hz, 1H), 7.74 (d, J = 8.8 Hz, 1H), 7.54 (d, J = 2.6 Hz, 2H), 7.49 (t, J = 8.1 Hz, 2H), 7.28 (t, J = 7.0 Hz, 1H), 7.17 (d, J = 8.2 Hz, 2H), 3.20 (s, 3H); FTIR(KBr) cm^-1: 3285, 1589, 1521; EI-MS m/z: 308 [M]⁺; HR-MS: Calcd for C₁₃H₁₂N₂O₅S [M]⁺: 308.0467. Found 308.0468.

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6807 - 6814

3
[ 121-88-0 ]
[ 51803-78-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6807 - 6814

4
[ 117346-07-3 ]
[ 51803-78-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6807 - 6814

5
[ 51765-51-6 ]
[ 51803-78-2 ]

Reference： [1] Organic Process Research and Development, 2002, vol. 6, # 6, p. 926 - 932

[ 51803-78-2 ] Synthesis Path-Downstream 1~69

1
[ 51803-78-2 ]
4-nitrosonimesulide [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 1421 - 1422

2
[ 51803-78-2 ]
N-(4-Cyano-2-phenoxy-phenyl)-methanesulfonamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 359 - 364

3
[ 51803-78-2 ]
N-[2-Phenoxy-4-(1H-tetrazol-5-yl)-phenyl]-methanesulfonamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1996,vol. 31,p. 359 - 364

4
[ 51803-78-2 ]
[ 543-20-4 ]
bis-(N-[(2-phenoxy-4-nitro)phenyl]-N'-methanesulfonyl)succinamide [ No CAS ]

Reference： [1]Patent: US6369260,2002,B1 .Location in patent: Example 11

5
[ 123-98-8 ]
[ 51803-78-2 ]
bis-(N-[(2-phenoxy-4-nitro)phenyl]-N'-methanesulfonyl)azelamide [ No CAS ]

Reference： [1]Patent: US6369260,2002,B1 .Location in patent: Example 12

6
[ 51803-78-2 ]
[ 251295-68-8 ]
N[(3-chloromethyl)benzoyloxymethyl]-N-(2-phenoxy-4-nitrophenyl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In THF (tetrahydrofuran) anhydrous; at 20℃; for 15h;	A solution of [CHLOROMETHYL] [3-CHLOROMETHYLBENZOATE] (1. [5 G,] 6. 80 m mol) i n anhydrous tetrahydrofurane (7 ml) was slowly added dropwise in a suspension of [N- (2-PHENOXY-4-] nitrophenyl) methanesulfonamide sodium salt (2.25 g, 6.80 [MMOL)] in anhydrous tetrahydrofurane (45 [MOI).] The reaction was allowed to stand overnight under stirring at room temperature. The solvent was evaporated at reduced pressure, the residue was dissolved in methylene chloride (60 [ML)] and the solution thus obtained was washed with a [5%] sodium bicarbonate solution and then with water. The organic phase was dried on sodium sulphate. The crude product thus obtained was purified by chromatography on a silica gel column with n-hexane/ethyl ether [7/3] as eluent to give 0.830 g of product 5A.

Reference： [1]Patent: WO2004/781,2003,A2 .Location in patent: Page 18-19

7
sodium N-(methylsulfonyl)-N-(4-nitro-2-phenoxyphenyl)sulfamate [ No CAS ]
[ 51803-78-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In water;pH ~ 2;	Moreover, Product I in which X is Na had a solubility in water of approximately 3.5 wt.% at room temperature. At this concentration, the aqueous solution was still stable on the seventh day at room temperature. Acidification of the solution to about pH 2 with HCl caused decomposition of the product and precipitation of the theoretical quantity of nimesulide

Reference： [1]Patent: EP1604976,2005,A1 .Location in patent: Page/Page column 4

8
[ 51803-78-2 ]
C₁₃H₁₂N₂O₈S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With alpha-picoline; chlorosulfonic acid; In dichloromethane; at -5 - 5℃; for 24.25h;Heating / reflux;	Chlorosulphonic acid (0.79 ml; 11.83 mmol) was added dropwise to a solution of 2-picoline (2.36 ml; 23.86 mmol) in anhydrous CH2Cl2 (10 ml) cooled to -5C, in such a way that the temperature was maintained at about 5C. The resulting solution was stirred for 15 minutes, still at a temperature in the range -5/5C. Then a solution of <strong>[51803-78-2]nimesulide</strong> (1 g; 3.25 mmol) in CH2Cl2 (6 ml) was added dropwise to the aforesaid solution. The reaction mixture was left under reflux for 24 h, and after cooling to room temperature it was washed with a buffer solution at pH = 4.6 [prepared by dissolving 4.54 g of NaH2PO4 in 250 ml of water and adjusting the pH by adding a solution of 0.1N NaOH] and the organic phase was evaporated. The solid residue was chromatographed on a column of silica gel (mesh 0.063-0.200), eluting with ethyl acetate. The fractions containing the product which, in thin-layer chromatography (silica gel F254), had Rf = 0.11 (eluent: ethyl acetate) were combined and evaporated at reduced pressure to give a solid residue consisting of Product I in which X is H.

Reference： [1]Patent: EP1604976,2005,A1 .Location in patent: Page/Page column 4

9
[ 107-59-5 ]
[ 51803-78-2 ]
[ 951238-70-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2: Preparation of N-(4-Nitro-2-phenoxy-phenyl) methanesulfonyl aniline acetic acid [Formula-IV]: i) Preparation of N-(4-Nitro-2-phenoxy-phenyl)methanesulfonyl aniline acetic acid t-butyl ester (D): (10 mmol) of Nimesulide was charged into 10 ml of dimethyl acetamide and stirred for 10 minutes at room temperature. (12 mmol) of sodium hydride was charged into the above solution and the solution was agitated for further 20 minutes at room temperature. (10 mmol) of t-butyl chloroacetate was charged into the above solution and the reaction mass was stirred at 50-60C for 15 hours. After stirring the extract, the product in ethyl acetate on recovery gave (8 mmol) of compound (D).

Reference： [1]Patent: WO2007/110876,2007,A2 .Location in patent: Page/Page column 22

10
[ 51803-78-2 ]
[ 116539-58-3 ]
[ 1309349-74-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 4: Nimesulide/(S)-duloxetine amorphous salt.; A solution of <strong>[51803-78-2]nimesulide</strong> (17.3 mg, 0.056 mmol, 1 eq) in 0.70 mL of methanol/tetrahydrofuran (8:2) was added to a solution of (S)-duloxetine (16.7 mg, 0.056 mmol, 1 eq) in 0.36 mL of methanol. The mixture was evaporated to dryness, and the residue obtained was dissolved in 1.3 mL of ethanol/water (1 :1 ) at 60C. The resulting solution was cooled to -21 C. After three weeks a dense oil was separated and dried under vacuum for 4 h at 40C to give a yellow solid corresponding to the <strong>[51803-78-2]nimesulide</strong>/(S)-duloxetine salt.The salt has also been obtained starting with a ratio of <strong>[51803-78-2]nimesulide</strong>/(S)-duloxetine of 1 :1 and 1 :2 in diisopropyl ether.Characterization of <strong>[51803-78-2]nimesulide</strong> / (S)-duloxetine amorphous salt'H NMR (400 MHz, d4-methanol) delta: 2.31-2.40 (m, 1 H), 2.50-2.59 (m, 1 H), 2.55 (s, 3H), 2.97 (s, 3H), 2.98-3.13 (m, 2H), 5.90 (dd, J = 8 Hz, J = 5 Hz, 1 H), 6.91-6.96 (m, 2H), 7.00-7.05 (m, 2H), 7.14-7.18 (m, 2H), 7.25 (t, J = 8 Hz, 1 H), 7.31 (dd, J = 5 Hz, J = 2 Hz, 1H), 7.34-7.40 (m, 3H), 7.44-7.49 (m, 2H), 7.52 (d, J = 3 Hz, 1 H), 7.64 (d, J = 9 Hz, 1H), 7.75-7.79 (m, 1 H), 7.92 (dd, J = 9 Hz, J = 3 Hz, 1 H), 8.25-8.29 (m, 1H).DSC (10C/min): A weak endothermic peak with an onset at 58C was observed (see figure 5)TG (10C/min): A weight loss of 0.5%, most probably corresponding to ethanol, was observed (see figure 5).XRPD (see figure 6)
	In tetrahydrofuran; methanol;Product distribution / selectivity;	Example 4: Nimesulide/(S)-duloxetine amorphous salt. A solution of <strong>[51803-78-2]nimesulide</strong> (17.3 mg, 0.056 mmol, 1 eq) in 0.70 mL of methanol/tetrahydrofuran (8:2) was added to a solution of (S)-duloxetine (16.7 mg, 0.056 mmol, 1 eq) in 0.36 mL of methanol. The mixture was evaporated to dryness, and the residue obtained was dissolved in 1.3 mL of ethanol/water (1:1) at 60C. The resulting solution was cooled to -21C. After three weeks a dense oil was separated and dried under vacuum for 4 h at 40C to give a yellow solid corresponding to the <strong>[51803-78-2]nimesulide</strong>/(S)-duloxetine salt. The salt has also been obtained starting with a ratio of <strong>[51803-78-2]nimesulide</strong>/(S)-duloxetine of 1:1 and 1:2 in diisopropyl ether.Characterization of <strong>[51803-78-2]nimesulide</strong> / (S)-duloxetine amorphous salt 1H NMR (400 MHz, d4-methanol) delta: 2.31-2.40 (m, 1H), 2.50-2.59 (m, 1H), 2.55 (s, 3H), 2.97 (s, 3H), 2.98-3.13 (m, 2H), 5.90 (dd, J = 8 Hz, J = 5 Hz, 1H), 6.91-6.96 (m, 2H), 7.00-7.05 (m, 2H), 7.14-7.18 (m, 2H), 7.25 (t, J = 8 Hz, 1H), 7.31 (dd, J = 5 Hz, J = 2 Hz, 1H), 7.34-7.40 (m, 3H), 7.44-7.49 (m, 2H), 7.52 (d, J = 3 Hz, 1H), 7.64 (d, J = 9 Hz, 1H), 7.75-7.79 (m, 1H), 7.92 (dd, J = 9 Hz, J = 3 Hz, 1H), 8.25-8.29 (m, 1H). DSC (10C/min): A weak endothermic peak with an onset at 58C was observed (see figure 5) TG (10C/min): A weight loss of 0.5%, most probably corresponding to ethanol, was observed (see figure 5). XRPD (see figure 6)

Reference： [1]Patent: WO2011/60962,2011,A1 .Location in patent: Page/Page column 18
[2]Patent: EP2332930,2011,A1 .Location in patent: Page/Page column 9

11
[ 51803-78-2 ]
[ 94-13-3 ]
[ 62-44-2 ]
[ 5422-92-4 ]
[ 99-76-3 ]
[ 99-96-7 ]

Reference： [1]Chemical Papers,2010,vol. 64,p. 405 - 408

12
[ 51803-78-2 ]
[ 5422-92-4 ]

Reference： [1]Chemical Papers,2010,vol. 64,p. 405 - 408

13
[ 7790-94-5 ]
[ 51803-78-2 ]
C₁₃H₁₂N₂O₈S₂ [ No CAS ]

Reference： [1]Molecular Pharmaceutics,2010,vol. 7,p. 1871 - 1876

14
[ 51803-78-2 ]
silver nitrate [ No CAS ]
[ 1364966-82-4 ]

Reference： [1]Polyhedron,2012,vol. 36,p. 112 - 119

15
[ 51803-78-2 ]
[ 1238644-23-9 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

16
[ 51803-78-2 ]
[ 1403656-19-8 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

17
[ 51803-78-2 ]
[ 1403656-20-1 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

18
[ 51803-78-2 ]
[ 1403656-21-2 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

19
[ 51803-78-2 ]
[ 1403656-22-3 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

20
[ 51803-78-2 ]
[ 1403656-23-4 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

21
[ 51803-78-2 ]
[ 1403656-24-5 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

22
[ 51803-78-2 ]
[ 1403656-25-6 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

23
[ 51803-78-2 ]
[ 1403656-26-7 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

24
[ 51803-78-2 ]
[ 1403656-27-8 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

25
[ 51803-78-2 ]
[ 1403656-28-9 ]

Reference： [1]Letters in drug design and discovery,2012,vol. 9,p. 742 - 748,7

26
[ 51803-78-2 ]
lead⁽²⁺⁾ cation [ No CAS ]
Pb⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

27
[ 51803-78-2 ]
cobalt(II) [ No CAS ]
Co⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

28
[ 51803-78-2 ]
nickel(II) [ No CAS ]
Ni⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

29
[ 51803-78-2 ]
copper(II) ion [ No CAS ]
Cu⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

30
[ 51803-78-2 ]
zinc(II) cation [ No CAS ]
Zn⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

31
[ 51803-78-2 ]
cadmium(II) [ No CAS ]
Cd⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

32
[ 51803-78-2 ]
tin(II) [ No CAS ]
Sn⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

33
[ 51803-78-2 ]
mercury ion [ No CAS ]
Hg⁽²⁺⁾*C₁₃H₁₂N₂O₅S [ No CAS ]

Reference： [1]Journal of Molecular Liquids,2013,vol. 182,p. 39 - 42

34
[ 51803-78-2 ]
2-(4-((4-chloro-3-methylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-(methylsulfonamido)-3-phenoxyphenyl)acetamide [ No CAS ]