[ CAS No. 526-08-9 ] {[proInfo.proName]}

Name: 526-08-9|4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide|98%
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SKU: A266126
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Quality Control of [ 526-08-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 526-08-9 ]

CAS No. :	526-08-9	MDL No. :	MFCD00057226
Formula :	C₁₅H₁₄N₄O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QWCJHSGMANYXCW-UHFFFAOYSA-N
M.W :	314.36	Pubchem ID :	5335
Synonyms :	Depocid;Depotsulfonamide;Inamil;Firmazolo;BRN-0308518;Raziosulfa;Plisulfan	Chemical Name :	4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide

Safety of [ 526-08-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 526-08-9 ]

* 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 [ 526-08-9 ]
Downstream synthetic route of [ 526-08-9 ]

[ 526-08-9 ] Synthesis Path-Upstream 1~1

1
[ 93880-94-5 ]
[ 526-08-9 ]

Reference： [1] Patent: US2858309, 1957, ,

[ 526-08-9 ] Synthesis Path-Downstream 1~88

1
[ 93880-94-5 ]
[ 526-08-9 ]

Reference： [1]Patent: US2858309,1957,

2
[ 4857-04-9 ]
[ 526-08-9 ]
[ 107090-12-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1298 - 1301

3
[ 2010-06-2 ]
[ 526-08-9 ]
[ 97854-94-9 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

4
[ 14625-39-9 ]
[ 526-08-9 ]
[ 107090-26-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1298 - 1301

5
[ 103740-34-7 ]
[ 526-08-9 ]
[ 97854-99-4 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

6
[ 57634-55-6 ]
[ 526-08-9 ]
[ 103726-73-4 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

7
[ 2103-99-3 ]
[ 526-08-9 ]
[ 97854-98-3 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

8
[ 2103-94-8 ]
[ 526-08-9 ]
[ 97854-97-2 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

9
[ 2104-04-3 ]
[ 526-08-9 ]
[ 97854-95-0 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

10
[ 15850-29-0 ]
[ 526-08-9 ]
[ 97854-96-1 ]

Reference： [1]Polish Journal of Chemistry,1985,vol. 59,p. 79 - 84

11
[ 14326-80-8 ]
[ 526-08-9 ]
[ 134144-04-0 ]

Reference： [1]Journal of the Indian Chemical Society,1990,vol. 67,p. 856 - 858

12
[ 1450-72-2 ]
[ 526-08-9 ]
[ 77544-98-0 ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 115 - 118

13
[ 1450-74-4 ]
[ 526-08-9 ]
[ 77544-99-1 ]

Reference： [1]Journal of the Indian Chemical Society,1981,vol. 58,p. 115 - 118

14
[ 526-08-9 ]
[ 141-97-9 ]
[ 116690-44-9 ]

Reference： [1]Journal of the Indian Chemical Society,1991,vol. 68,p. 415 - 416

15
[ 526-08-9 ]
[ 118-93-4 ]
4-<5-(1-phenylpyrazolyl)sulphamyl>-2'-hydroxy-α-methylbenzylideneaniline [ No CAS ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1981,vol. 20,p. 853 - 855

16
[ 526-08-9 ]
[ 93073-06-4 ]
[ 93072-85-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 483 - 485

17
[ 526-08-9 ]
[ 90-02-8 ]
[ 61732-88-5 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 511 - 516

18
[ 526-08-9 ]
[ 90-02-8 ]
4-<5-(1-phenylpyrazolyl)sulphamyl>-2'-hydroxybenzylideneaniline [ No CAS ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1981,vol. 20,p. 853 - 855

19
[ 526-08-9 ]
[ 99876-68-3 ]
[ 107090-19-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 1298 - 1301

20
[ 526-08-9 ]
[ 123-54-6 ]
[ 41095-22-1 ]

Reference： [1]Journal of the Indian Chemical Society,1991,vol. 68,p. 415 - 416

21
[ 526-08-9 ]
[ 708-06-5 ]
2-hydroxy-1-naphthaldehyde sulphaphenazine [ No CAS ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 157 - 161
[2]Journal of the Indian Chemical Society,1982,vol. 59,p. 800 - 801

22
[ 6270-08-2 ]
[ 526-08-9 ]
4-(2,6-Dimethyl-quinolin-4-ylamino)-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 871 - 873

23
[ 53342-53-3 ]
[ 526-08-9 ]
4-(6-Chloro-2-methyl-quinolin-4-ylamino)-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 871 - 873

24
[ 50593-73-2 ]
[ 526-08-9 ]
4-(6-Methoxy-2-methyl-quinolin-4-ylamino)-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 871 - 873

25
[ 64951-58-2 ]
[ 526-08-9 ]
4-(8-Methoxy-2-methyl-quinolin-4-ylamino)-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 871 - 873

26
[ 19602-82-5 ]
[ 526-08-9 ]
C₄₄H₃₄N₈O₆S₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 67 - 86

27
[ 526-08-9 ]
[ 126-81-8 ]
4-[N'-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-hydrazino]-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1997,vol. 74,p. 480 - 482

28
[ 526-08-9 ]
[ 6328-58-1 ]
4-(4-hydroxy-6-methyl-2-methylsulfanyl-pyrimidin-5-ylazo)-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1997,vol. 74,p. 480 - 482

29
[ 526-08-9 ]
[ 97-51-8 ]
Sulphaphenazole 5-nitrosalicylaldimine [ No CAS ]

Reference： [1]Revue Roumaine de Chimie,1992,vol. 37,p. 433 - 438

30
[ 526-08-9 ]
[ 635-93-8 ]
Sulphaphenazole 5-chlorosalicylaldimine [ No CAS ]

Reference： [1]Revue Roumaine de Chimie,1992,vol. 37,p. 433 - 438

Yield	Reaction Conditions	Operation in experiment
		Representative examples include, but are not limited to: ... sulfamoxole sulfanilamidomethanesulfonic acid triethanolamine salt sulfanilic acid sulfanitran sulfaphenazole sulfapyrazine sulfapyridine sulfaquinoxaline ...

33
[ 526-08-9 ]
[ 87-13-8 ]
C₂₃H₂₄N₄O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 135℃; for 1.0h;	EXAMPLE 47 N-[(4-Chlorophenyl)methyl]-4-hydroxy-6-[[(1-phenyl-1H-pyrazol-5-yl)amino]sulfonyl]-3-quinolinecarboxamide [] A solution of sulfapyridine (6.23 g) and diethyl ethoxymethylenemalonate (5.406 g) is heated to 135C for 1 h. The mixture is cooled to room temperature. Diphenyl ether (50 mL) is added and the mixture is heated to 250 C for 30 min. The mixture is cooled to room temperature and poured into 250 mL hexanes. An oily residue formed and the solvents are decanted off. The residue is taken up in CH2Cl2. Hexanes are added and a solid formed which is collected and dried. The solid is chromatographed on silica, eluting with 5% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and concentrated in vacuo to yield 0.254 g of the desired ester as a pale-yellow solid. A mixture of this ester (0.200 g) and 4-chlorobenzylamine (0.28 mL) are heated to 180 C for 1 h. The reaction is cooled to room temperature and diluted with CH2Cl2. The resulting solid is collected, dried and chromatographed on silica, eluting with 5% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and concentrated in vacuo. The resulting solid is recrystallized from acetone/hexanes to yield 0.031 g of the desired product as a tan solid. Physical characteristics are as follows: Mp 185-187 C.IR (mull) 3251, 3089, 3066, 1652, 1624, 1612, 1598, 1553, 1521, 1502, 1338, 1166, 760, 692, 683 cm-1.MS (FAB) m/z 534 (MH+), 536, 535, 534, 160, 142, 139, 125, 123, 105, 103.HRMS (FAB) found 534.1023.

Reference： [1]Patent: EP1042295,2005,B1 .Location in patent: Page/Page column 58

34
[ 25784-91-2 ]
[ 526-08-9 ]
[ 372094-83-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 2,4-dichlorophenoxyacetic acid dimethylamine;	Example 108 N-[4-[(2-Phenyl-(2H)-pyrazol-3-yl)aminosulfonyl]phenyl]-(2-chloro-5-nitrophenyl)carboxamide The title compound (0.428 g, yield 86%) was obtained according to the procedure described in Example 2 using <strong>[526-08-9]sulfaphenazole</strong> (0.314 g, 1.0 mmol, a product of Tokyoksei), DMA (2.5 ml) and 2-chloro-5-nitrobenzoyl chloride (0.264 g, 1.2 mmol). Rf 0.63 [methylene chloride:methanol=7:1 (v/v)]; 1H-NMR (400 MHz, DMSO-d6,TMS): delta(ppm) 5.89 (1H, d, J=1.8 Hz), 7.40 (1H, m), 7.48 (4H, m), 7.59 (1H, d, J=1.8 Hz), 7.69 (2H, d, J=8.8 Hz), 7.85 (2H, d, J=8.8 Hz), 7.93 (1H, d, J=8.8 Hz), 8.37 (1H, dd, J=2.9, 8.8 Hz), 8.56 (1H, d, J=2.9 Hz), 11.13 (1H, s); MS(FAB) m/z: 498 (M+H)+.

Reference： [1]Patent: US2003/134859,2003,A1

35
[ 1148108-83-1 ]
[ 526-08-9 ]
[ 1148108-98-8 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2008,vol. 183,p. 2541 - 2554

36
[ 463-71-8 ]
[ 526-08-9 ]
[ 1148108-83-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; for 1.0h;	Sulfaphenazole 1 (0.01 mol) was dissolved in 100 ml H2Ocontaining 20 ml of concentrated HCl. To this, 0.012 mol ofCSCl2 was added in one portion. Stirring was begunimmediately and continued until all of the red color ofCSCl2 disappeared (1 h) and the product was precipitated asa white crystal. The resulting solid was filtered off, driedand recrystallized from acetone to give 2 (Ismail et al.2008).

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2008,vol. 183,p. 2541 - 2554
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2010,vol. 185,p. 211 - 221
[3]Arzneimittel-Forschung/Drug Research,2009,vol. 59,p. 666 - 671
[4]Medicinal Chemistry Research,2018,vol. 27,p. 72 - 79

37
[ 526-08-9 ]
[ 79-04-9 ]
2-chloro-N-(4-(N-(1-phenyl-1H-pyrazol-5-yl)-sulfamoyl)phenyl)acetamide [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2009,vol. 59,p. 666 - 671
[2]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

38
[ 526-08-9 ]
[ 105-56-6 ]
[ 1214261-59-2 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2009,vol. 59,p. 666 - 671
[2]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

39
[ 526-08-9 ]
[ 109-77-3 ]
[ 1214261-57-0 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2009,vol. 59,p. 666 - 671
[2]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

40
[ 526-08-9 ]
[ 1214261-54-7 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

41
[ 526-08-9 ]
[ 1332624-92-6 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

42
[ 526-08-9 ]
[ 1332624-93-7 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

43
[ 526-08-9 ]
[ 1332624-94-8 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

44
[ 526-08-9 ]
[ 1332624-95-9 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

45
[ 526-08-9 ]
[ 1332624-96-0 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

46
[ 526-08-9 ]
[ 1332624-97-1 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

47
[ 526-08-9 ]
[ 1332624-98-2 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

48
[ 526-08-9 ]
[ 1332624-91-5 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 935 - 941

49
[ 86-98-6 ]
[ 526-08-9 ]
[ 1449365-38-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 50 - 58

50
[ 1379522-28-7 ]
[ 526-08-9 ]
[ 1432024-35-5 ]

Yield	Reaction Conditions	Operation in experiment
89.3%	With acetic acid; for 15.0h;Reflux;	General procedure: In a flask fitted with a reflux IIa-h (10 mmol) and the corresponding starting aromatic amine (10 mmol) were mixed in an anhydrous acetic acid atmosphere (7 mL). The mixture was boiled for 15 h, cooled to room temperature; 5 mL of light petroleum was added. The precipitated crystals were filtered, washed with ether and dried.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2696 - 2703

51
[ 346-55-4 ]
[ 526-08-9 ]
[ 1489236-23-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	In N,N-dimethyl-formamide; for 12.0h;Reflux;	General procedure: A mixture of 1 (2.31 g, 0.01 mol) and the corresponding sulfadrugs (0.012 mol) in dry DMF (20 mL) was refluxed for 12 h. The solid obtained after concentration was filtered and crystallized from dioxane to give 2-14, respectively.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 373 - 383

52
[ 16024-82-1 ]
[ 526-08-9 ]
methyl 2-(3-(4-(N-(1-phenyl-1H-pyrazol-5-yl)sulfamoyl)phenyl)thioureido)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol; at 20℃; for 5.0h;	A mixtureof compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (3.14 g, 0.01 mole) in absolute ethanol (30 mL) was stirred at room temperature for 5 h. The reaction mixture was poured onto ice water and the solid obtained was recrystallized from dioxane to give 3. Yield% 88; m.p. 322.9 C; IR (KBr, nmax, Cm-1): 3448, 3275(NH),3039 (CH arom.), 2977, 2863 (CH aliph.), 1662 (C=O), 1620(C=N), 1342, 1168 (SO2), 1261 (C=S). 1H NMR spectrum in(DMSO-d6): 4.21 [s, 3H, OCH3], 6.60, 7.64 [2d, 2H, 2CHpyrazole, J = 7.33 Hz], 7.08- 8.12 [m, 13H, Ar-H], 11.46 [s,1H, SO2NH, D2O-exchangeable], 12.95 [s, 2H, 2NH, D2O exchangeable].13C NMR spectrum (in DMSO-d6): 52.4, 95.6,121.3 (2), 121.8, 127.9 (2), 128.5 (2), 129.0 (2), 131.4, 132.6,134.3, 137.8, 139.6, 141.2, 141.8, 144.9, 168.1, 181.2. Anal.Calc. for C24H21N5O4S2 (508): C, 56.79; H, 4.17; N, 13.80;found: C, 56.42; H, 4.34; N, 13.49.

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 8501 - 8504

53
[ 16024-82-1 ]
[ 526-08-9 ]
4-(4-oxo-2-thioxo-1,2-dihydroquinazolin-3(4H)-yl)-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In ethanol; for 18.0h;Reflux;	A mixture of compound 2 (1.93 g, 0.01 mole) and 4-amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (3.14 g, 0.01 mole) in absolute ethanol (30 mL) containing a catalytic amount of triethylamine was refluxed for 18 h. The reaction mixture was cooled and poured onto ice water and the solid obtained was recrystallized from dioxane to give 4. Yield % 90; m.p. 300.4 C; IR (KBr, nmax, Cm-1): 3307, 3210(NH), 3088 (CH arom.), 1688 (C=O), 1610 (C=N), 1365, 1155(SO2), 1272 (C=S). 1H NMR spectrum (in DMSO-d6): 6.44,7.41 [2d, 2H, 2CH pyrazole, J = 6.97 Hz], 7.05-8.23 [m, 13H,Ar-H], 9.35 [s, 1H, NH, D2O-exchangeable], 11.44 [s, 1H,SO2NH, D2O-exchangeable]. 13C NMR spectrum (in DMSOd6):91.7, 119.8 (2), 120.6 (2), 122.7, 124.6, 125.1, 126.8 (2),127.6, 127.9, 128.5 (2), 130.6, 134.1, 134.7, 140.4, 141.3,141.9, 144.8, 162.7, 187.3. Anal. Calc. for C23H17N5O3S2 (476):C, 58.09; H, 3.60; N, 14.73; found: C, 58.32; H, 3.31; N, 14.51.

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 8501 - 8504

54
[ 6484-25-9 ]
[ 526-08-9 ]
N-(1-phenyl-1H-pyrazol-5-yl)-4-(2-phenylquinazolin-4-ylamino)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In N,N-dimethyl-formamide; for 22.0h;Reflux;	General procedure: A mixture of 4-chloro-2-phenylquinazoline (1, 2.42 g, 0.01 mol) and sulfonamides (0.012 mol) in dry dimethylformamide (10 mL) was refluxed for 22 h., then left to cool. The solid product formed upon pouring onto ice/water was collected by filtration and recrystallized from ethanol-dimethylformamide to give 2-18, respectively.

Reference： [1]Molecules,2016,vol. 21

55
[ 33987-02-9 ]
[ 526-08-9 ]
4-(benzo[g]quinazolin-4-ylamino)-N-(1-phenyl-1Hpyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine; In N,N-dimethyl-formamide; for 24.0h;Reflux;	General procedure: A mixture of 4-chlorobenzo[g]quinazoline 1 (2.15g, 0.01mmol) and sulfonamides (0.012 mmol) in dry DMF (15mL)was refluxed for 24h., then left to cool. The solid productformed upon pouring onto ice/ water was collected by filtrationand recrystallized from ethanol- DMF to give 2-18, respectively.

Reference： [1]Medicinal Chemistry,2016,vol. 12,p. 448 - 456

56
[ 28900-10-9 ]
[ 526-08-9 ]
4-(3-cyano-6-methylpyridin-2-ylamino)-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine; In N,N-dimethyl-formamide; for 18.0h;Reflux;	General procedure: A mixture of 2-chloro-6-methylnicotinonitrile (II)(1.52 g, 0.01 mol) and corresponding sulfonamide derivatives (0.012 mol) in dry dimethylformamide(10 mL) containing 3 drops of trimethylamine was refluxed for 18 h then left to cool. The solid productformed upon pouring onto ice water was collected byfiltration and recrystallized from ethanol-dimethylformamide to give (III-XX), respectively.

Reference： [1]Russian Journal of Bioorganic Chemistry,2016,vol. 42,p. 441 - 448

57
[ 526-08-9 ]
[ 613-94-5 ]
[ 4637-24-5 ]
N-(1-phenyl-1H-pyrazol-5-yl)-4-(3-phenyl-4H-1,2,4-triazol-4-yl) benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With acetic acid; In acetonitrile; for 9.0h;Reflux;	General procedure: A mixture of benzoylhydrazine (1.22 g, 0.01mol), dimethylformamide-dimethylacetal (1.91 g,0.01 mol)) and sulfa-drugs (0.012 mol) in dry acetonitrile(15 mL) containing acetic acid (3 mL) was refluxed for 9 h., then left to cool. The solid product formed was collected by filtration and recrystallized from dioxane to give compounds 1-13, respectively.

Reference： [1]Acta poloniae pharmaceutica,2016,vol. 73,p. 1147 - 1153

58
[ 526-08-9 ]
[ 371756-61-5 ]
(Z)-4-(3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-enylamino)-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	In ethanol; for 21.0h;Reflux;	General procedure: 5.1.2.1. General procedure. A mixture of 2 (1.88 g, 0.01 mol) and sulfa-drugs (0.012 mol) in absolute ethanol (10 mL) and glacial acetic acid (5 mL) was refluxed for 21 h, then left to cool. The solid product formed was collected by filtration and recrystallized from ethanol-dimethylformamide to give 3-20.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 124,p. 946 - 958

59
[ 127172-22-9 ]
[ 526-08-9 ]
Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(1-phenyl-1H-pyrazol-5-yl)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With acetic acid; In ethanol; for 22.0h;Reflux;	General procedure: General ProcedureA mixture of 2 (2.35 g, 0.01 mol) and sulfa drugs (0.012 mol) in absolute ethanol (10 mL) and glacial acetic acid (5 mL) was refluxed for 22h, and subsequently left to cool. The solid product formed was collected by filtration and recrystallized from acetic acid to give compounds 3-19.

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 1747 - 1754

60
[ 526-08-9 ]
(Z)-3-(dimethylamino)-1-(10H-phenothiazin-2-yl)prop-2-en-1-one [ No CAS ]
(Z)-4-(3-oxo-3-(10H-phenothiazine-2-yl)prop-1-enylamino)-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol; for 18.0h;Reflux;	General procedure: A mixture of 3 (2.96g, 0.01mol) and sulfa drugs 4 (0.012mol) in absolute ethanol (10mL) and glacial acetic acid (3mL) was refluxed for 18h. The solid product formed was collected by filtration and crystallized from ethanol to give 5-22.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 134,p. 304 - 315

61
[ 526-08-9 ]
N1-phenyl-N2-(4-(N-(1-phenyl-1H-pyrazol-5-yl)sulfamoyl)phenyl)hydra-zine-1,2-bis (carbothioamide) [ No CAS ]