Name: 80-08-0|4,4'-Sulfonyldianiline|98%
Brand: Ambeed
SKU: A240646
Price: 5.0 USD
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1
[ 85-44-9 ]
[ 80-08-0 ]
[ 149131-31-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	In methanol; at 65℃; for 4h;	General procedure: To a solution of isobenzofuran-1,3-dione (1.48 g, 10 mmol) in methanol (4 mL/1 mmol) at room temperature was added aliphatic or aromatic amine (10 mmol) and the reaction mixture was refluxed at 65 C for 4 h. After completion of the reaction as indicated by the TLC, the reaction was cooled to room temperatureand purified by column chromatography using petroleum ether:ethyl acetate (7:3).

Reference： [1]Asian Journal of Chemistry,2019,vol. 31,p. 2548 - 2556
[2]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 3795 - 3799
[3]Journal of the Chemical Society,1942,p. 42,45
[4]Journal of the Chemical Society,1942,p. 42,45
[5]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3084 - 3087

2
[ 80-07-9 ]
[ 80-08-0 ]

Yield	Reaction Conditions	Operation in experiment
91.9%	With ammonium chloride; In ethanol; for 5h;Reflux;	50.0 ml of ethanol was taken in a 250 ml three-necked flask, And then slowly adding <strong>[80-07-9]4,4'-dichlorodiphenylsulfone</strong> 10.0 g (40.27 mmol), 4.30 g (80.54 mmol) of ammonium chloride solid, while stirring while adding 50.0 ml of ethanol, heating reflux reaction 5h, TLC point The reaction was completed, 30ml of distilled water slowly quenched the reaction, stirring cooling, to be a large number of solid precipitation, filtration, with a small amount of ethanol washing filter cake three times, at 40 blast drying, to obtain white crystalline powder 7.9g, Yield: 91.9%.
	With ammonium hydroxide; copper(I) bromide; at 200℃; for 40h;	Into the copper liner of an Adkins rocking bomb is placed 20 g. of 4,4'- dichlorodiphenyl sulfone, 1 g. of cuprous bromide, 0.5 g. copper bronze and 170 cc. of 28% aqueous ammonia. The bomb is shaken at 200 for about 40 hours and shaking is continued during the cooling period to avoid solidification of the product as a solid cake. The solid is filtered from the ammoniacal liquid, washed with water, and dissolved in 10% hydrochloric acid. A small amount of tar and the copper bronze are removed by treatment with Darco activated carbon and filtration. The solution is cooled and the clear brownish liquid is basified with ammonia. The collected precipitate is washed with ammonium hydroxide and water and dissolved in 150 cc. of ethanol and 50 cc. of water. A voluminous precipitate of ferric hydroxide is left undissolved, and it is filtered with addition of standard Super Cel calcined diatomaceous earth filter aid. The slightly brownish filtrate is clarified with Darco activated carbon and diluted with boiling water to a volume of about 800 cc. Flat needles of 4,4'- diaminodiphenylsulfone crystallize on cooling.

Reference： [1]Patent: CN106518735,2017,A .Location in patent: Paragraph 0011
[2]Journal of the American Chemical Society,1945,vol. 67,p. 1979,1985
[3],1944,vol. 26,p. 7
[4]Patent: DE735415,1941,
DRP/DRBP Org.Chem.,
[5]Patent: FR829926,1937,
[6]Patent: WO2019/30184,2019,A1 .Location in patent: Page/Page column 21

3
[ 80-07-9 ]
[ 7146-68-1 ]
[ 80-08-0 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 209 - 210
    Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 234 - 235
[2]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 209 - 210
    Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 234 - 235
[3]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 209 - 210
    Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 234 - 235
[4]Chimica e l'Industria (Milan, Italy),1944,vol. 26,p. 7

4
[ 77-46-3 ]
[ 80-08-0 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of N,N'-diamino-diphenyl sulfone N,N'-Diamino-diphenyl sulfone can be synthesized in various ways, but the following synthesis route is offered as an example. This synthesis was performed in two steps: 1. 60 g of acetanilide were poured into an Erlenmeyer flask and heated slowly with flame until the melting of the solid was complete. The resulting viscous liquid was cooled in a glass of ice, ensuring that the solidified material stayed at the bottom of the flask. 165 ml of chloro-sulfonic acid were added in a single portion, without removal from the ice bath. Subsequently, the flask was removed from the ice, mixing carefully, and the reaction was allowed to be take place for 10 minutes, at the end of which the reaction mixture was again heated until the total solubilization of the remaining acetanilide, allowing it to react again for 10 more minutes. The product was allowed to cool and was carefully poured into a container with ice and water, filtering the precipitate and washing it with cold water. The precipitate was collected, dissolved in chloroform and extracted three times with water, collecting the chloroform phase, which was placed in an ice bath, precipitating the purified thionyl chloride (Reported melting point of the intermediary: 149C). 2. 123.6 ml of anhydrous nitrobenzene were poured into a glass reactor, 89.2 g of aluminum chloride were added and heated slowly; then, 41.3 g of thionyl chloride was added to the hot mixture, heating the reaction mixture at a temperature of 140 - 145 C, and 13 g of acetanilide were slowly added, maintaining the reaction temperature for two hours. At the end of this period, the product of the reaction was poured into 104 ml of water acidified with hydrochloric acid then dark crystals were precipitated, and were recrystallized with dilute acetic acid. These crystals were refluxed with 5N hydrochloric acid for 30 minutes, then neutralizing the reaction mixture, with which white crystals were precipitated (raw DDS), which was recrystallized again with ethanol.
114 g	With hydrogenchloride; In water; at 100℃; for 6h;	Oxidation:In a 5L three-necked flask with mechanical stirring, 4,4'-bis (N-acetyl) diphenylsulfoxide (Compound 1,158 g, 500 mmol) was dissolved in 2000 ml of isopropanol, and then added A copper complex catalyst (CuL2-Cat.) (2.8 g, 7.5 mmol) was used as a catalyst. Under agitation conditions, oxygen was continuously introduced and a catalytic oxidation reaction was performed at 80 C. After stirring for 24 hours, the reaction was completed. The reaction was lowered to room temperature, and CuL2-Cat. Was separated by filtration. The filtrate was concentrated under reduced pressure to remove the isopropanol solvent. After vacuum drying, 4,4'-bis (N-acetyl) di Phenylsulfone (compound 2), all solids were used directly in the next hydrolysis reaction.Hydrolysis reaction: Suspend the solid obtained in the above reaction in 1000 ml of a 2.0 mol / L hydrochloric acid solution, and then raise the temperature of the reaction solution to 100 C. and stir for 6 hours. After the hydrolysis is completed, reduce to room temperature and use 10% (mass) Fractional) sodium hydroxide solution adjusted the pH of the solution to 12, and precipitated a large amount of solids. The product was filtered and washed with water to obtain a crude 4,4'-diaminodiphenylsulfone, which was a crude 4,4'-diaminodiphenylsulfone. After recrystallization from acetone, 114 g of a white solid was obtained, which was pure 4,4'-diaminodiphenylsulfone (compound 3). The yield was 92% in two consecutive steps.

Reference： [1]Journal of labelled compounds and radiopharmaceuticals,2003,vol. 46,p. 107 - 114
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 68,71
    Chem.Abstr.,1948,p. 723
[3]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 55,58, 60
    Chem.Abstr.,1948,p. 723
[4]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 55,58, 60
    Chem.Abstr.,1948,p. 723
[5]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1922,vol. 174,p. 168
[6]Patent: EP2425829,2012,A1 .Location in patent: Page/Page column 3
[7]Patent: CN110590671,2019,A .Location in patent: Paragraph 0019; 0053-0060

5
[ 565-20-8 ]
[ 80-08-0 ]

Yield	Reaction Conditions	Operation in experiment
5 mg	With water; sodium hydroxide; In methanol; at 35℃; for 2h;	In a reaction flask 10 mg of N-(4-(4-aminophenylsulfonyl)phenyl)acetamide (0.00008 mol), 2 ml di methanol, 1 ml of water and 6 mg of NaOH (0.00016 mol) were charged, the temperature was brought to about 35C and the reaction mixture was kept under in these conditions for about 2 hours. At the end of the reaction, 2 ml of ethyl acetate were added, the aqueous phase was extracted with ethyl acetate (1 x 1 ml), and the collected organic phases were reduced to a residue by distillation under vacuum to give 5 mg of Dapsone.

Reference： [1]Journal of the American Chemical Society,1941,vol. 63,p. 1930,1931
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 68,71
    Chem.Abstr.,1948,p. 723
[3]Arzneimittel-Forschung/Drug Research,1989,vol. 39,p. 1081 - 1084
[4]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 68,71
    Chem.Abstr.,1948,p. 723
[5]Patent: WO2016/16321,2016,A1 .Location in patent: Page/Page column 11
[6]Patent: DE740445,1937,
    DRP/DRBP Org.Chem.,

6
[ 6626-22-8 ]
[ 80-08-0 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 1925,1928

7
[ 108-24-7 ]
[ 80-08-0 ]
[ 565-20-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine; dmap; at 20℃; for 10h;	To a solution of 4,4'-sulfonyldianiline (283 mg, 1.1 mmol, 3 equiv.) in pyridine (1 mL) was added Ac2O (36 muL, 0.38 mmol, 1 equiv.) and catalytic amounts of DMAP and the reaction stirred for 10 h at RT. Column chromatography on silica gel (DCM/MeOH) afforded the desired product as a white solid (100 mg, 0.034 mmol, 88%). Rf=0.51 (DCM/MeOH, 10:1). LC-MS: m/z=291.05 [M+H]+. 1H NMR (DMSO-d6, 400 MHz) delta ppm 10.31 (s, 1H), 7.70-7.77 (m, 2H), 7.50 (d, J=8.8 Hz, 2H), 6.60 (d, J=8.8 Hz, 2H), 6.13 (s, 2H), 2.06 (s, 3H). 13C NMR (DMSO-d6, 101 MHz) delta ppm 169.0, 153.4, 142.9, 136.8, 129.2, 127.7, 126.1, 118.8, 112.9, 24.1, 22.8.

Reference： [1]Patent: US2020/123130,2020,A1 .Location in patent: Paragraph 0124
[2]Journal of the American Chemical Society,1943,vol. 65,p. 2375

8
[ 141-75-3 ]
[ 80-08-0 ]
N-[4-[4-(butanoylamino)phenyl]sulfonylphenyl]-butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With pyridine; In 1,4-dioxane; at 20℃;	General procedure: Dapsone (3 mmol) is dissolved in pyridine (5 mL/mmol). The acyl chloride (1 mmol) is dissolved in dioxane (5 mL/mmol) and added dropwise to the reaction mixture which is then stirred over night at room temperature. To purify the crude product, approximately 50 mL of diethylether are added to the solution. The formed precipitate is separated and dissolved in DMF. The solution is poured into 200 mL of 2 M hydrochloric acid and the resulting precipitate is filtered off and washed thoroughly with water. The product is dried in vacuo and can be further purified by flash column chromatography.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3717 - 3731
[2]Zhurnal Obshchei Khimii,1947,vol. 17,p. 471,474
Chem.Abstr.,1948,p. 534

9
[ 79-04-9 ]
[ 80-08-0 ]
[ 17328-16-4 ]

Yield	Reaction Conditions	Operation in experiment
12.5%	With triethylamine; In acetone; at 20℃;Cooling with ice;	General procedure: Mono-chloromethyl-acetamido- derivatives were preparedas described earlier [24]. Briefly: To a magneticallystirred, ice-bathed, solution or suspension of the particularcommercially available sulfanilamide or aniline (1.0 equivalent)and triethylamine (2.0 equivalents) in dry acetone (25ml), chloroacetylchloride (1.5 equivalents) in dry acetone (25ml) was gradually added over 30 minutes. The reaction mixturewas stirred at room temperature until TLC revealedcomplete consumption of the starting amine. Subsequently,the reaction mixture was poured slowly onto ice water (100ml). The precipitated crude products were purified by recrystallizationfrom acetone/water. Scheme 1 shows the preparedcompounds and their corresponding starting materials.
6%	With pyridine; In 1,4-dioxane; at 20℃;	General procedure: Dapsone (3 mmol) is dissolved in pyridine (5 mL/mmol). The acyl chloride (1 mmol) is dissolved in dioxane (5 mL/mmol) and added dropwise to the reaction mixture which is then stirred over night at room temperature. To purify the crude product, approximately 50 mL of diethylether are added to the solution. The formed precipitate is separated and dissolved in DMF. The solution is poured into 200 mL of 2 M hydrochloric acid and the resulting precipitate is filtered off and washed thoroughly with water. The product is dried in vacuo and can be further purified by flash column chromatography.

Reference： [1]Medicinal Chemistry,2020,vol. 16,p. 403 - 412
[2]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 3717 - 3731
[3]Proceedings - Indian Academy of Sciences, Section A,1950,vol. 31,p. 21,22
[4]Journal of the American Chemical Society,2005,vol. 127,p. 12434 - 12435

10
[ 590-92-1 ]
[ 80-08-0 ]
[ 114769-68-5 ]

Reference： [1]Patent: US2399600,1943,

11
[ 64-18-6 ]
[ 80-08-0 ]
[ 6784-25-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With Na+-MMT-[pmim]HSO4; In neat (no solvent); at 60℃; for 0.416667h;	General procedure: Amine (1 mmol) was added to a mixture of Na+-MMT-[pmim]HSO4 (10 mg, 1 mol %) and formic acid (2 mmol) and the resulting mixture was stirred at 60 C for the appropriate time. After completion of the reaction (monitored by TLC), ethyl acetate (10 mL) was added and the catalyst was separated by filtration. The organic phase was washed with water (2 x 10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the desired product.
	In toluene; for 8h;Reflux;	General procedure: General procedure for the isonitrile synthesis: The mixture of diamine 1 (0.050 mol), toluene (100 ml) and 98% formic acid (7.5 ml, 0.2 mol) was refluxed for 8 h. After cooling, the mixture was evaporated to dryness, the residue was treated with a new portion of toluene (100 ml) and evaporated again to give the crude diformamide 2. To a flask with crude diformamide 2 was added triethylamine (51 ml, 0.36 mol) and dichloromethane (200 ml). The resulting solution (or suspension) of crude diformamide 2 was cooled to 0oC (ice-water bath) and phosphorous oxychloride (11.3 ml, 0.12 mol) was added dropwise over 20-30 minutes. After the addition of the POCl3, the mixture was stirred for about 1 h at 0oC (ice-water bath) and 2 h at room temperature. The reaction mixture was cooled again (0oC, ice-water bath) and a solution of about 25 g of Na2CO3 in 100 ml of water was added dropwise over 15-20 minutes. The final two-phase mixture was stirred for about 1 h. The organic phase was separated and the aqueous phase was extracted with dichloromethane (3×50 ml). The combined organics were washed with brine (4×50 ml), dried over anhydrous Na2SO4, and concentrated in vacuo, yielding crude isocyanide 3.The oily isocyanide 3m was used for the next step without purification, 3l was purified by bulb to bulb distillation, while the remaining solid isocyanides were crystallized from an appropriate solvent (see Table 1 at page 3). 1,6-Diisocyanohexane was purchased from Sigma-Aldrich, Germany. Isocyanides 3a,3-6 3b,5-7 3c,7 3d,7-9 3e,4,10 3f,7 3g,4,11,12 3h,12,13 3j,4,7 3k,14,15 and 3m9,16 are known in the literature. Spectroscopic data for the new isocyanides 3i and 3l are shown below.

Reference： [1]Research on Chemical Intermediates,2016,vol. 42,p. 1759 - 1776
[2]Zhurnal Obshchei Khimii,1947,vol. 17,p. 471,474
Chem.Abstr.,1948,p. 534
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3475 - 3479

12
[ 870-72-4 ]
[ 80-08-0 ]
[ 5533-30-2 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 617

13
[ 80-08-0 ]
[ 7300-27-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; sodium nitrite; In hydrogenchloride; water;	4-Azidophenyl sulfone A solution of NaNO2 (0.48 g, 7.00 mmol) in water was added dropwise to a solution of 4-aminophenyl sulfone (0.83 g, 3.33 mmol) in 2 N HCl (14 mL) at 0-5 C. with vigorous stirring. The mixture was kept below 5 C. for 30 min followed by neutralization with calcium carbonate. Then, a solution of NaN3 (0.49 g, 7.53 mmol) in water (3 mL) was added dropwise while the temperature was kept below 5 C. The solid precipitate was filtered, washed with water (3*30 mL) and finally recrystallized from ethanol. Yield: 2.73 mmol, 82%, yellow solid. 1H: [300 MHz, CDCl3] delta=7.10-7.13 (m, 4H), 7.89-7.91 (m, 4H) ppm. 13C: [75 MHz, CDCl3] delta=119.7, 129.5, 137.6, 145.4 ppm. MS-EI: [C11H8N6O2S] m/z cal. [M]+·=300.0429, m/z found [M]+·=300.0429.

Reference： [1]Organic Preparations and Procedures International,2011,vol. 43,p. 451 - 455
[2]Journal of the American Chemical Society,2005,vol. 127,p. 12434 - 12435
[3]Journal of the American Chemical Society,1948,vol. 70,p. 1268
[4]Monatshefte fur Chemie,1950,vol. 81,p. 970,972, 978
[5]Patent: US2009/92980,2009,A1

14
[ 513-08-6 ]
[ 80-08-0 ]
[ 125927-27-7 ]

Yield	Reaction Conditions	Operation in experiment
	In diethylene glycol dimethyl ether Heating;
	In diethylene glycol dimethyl ether for 15h; Heating;

Reference： [1]Simon, John D.; Su, Shyh-Gang [Journal of Physical Chemistry, 1990, vol. 94, # 9, p. 3656 - 3660]
[2]Simon, John D.; Doolen, Robert [Journal of the American Chemical Society, 1992, vol. 114, # 12, p. 4861 - 4870]

15
[ 80-08-0 ]
[ 108-95-2 ]
[ 89304-92-7 ]

Reference： [1]Russian Journal of General Chemistry,2014,vol. 84,p. 1629 - 1633
[2]Journal of the American Chemical Society,2010,vol. 132,p. 5542 - 5543
[3]Journal of Materials Chemistry,2008,vol. 18,p. 5019 - 5026
[4]Reactive and functional polymers,2010,vol. 70,p. 616 - 621
[5]Journal of the Indian Chemical Society,1993,vol. 70,p. 182 - 183

16
[ 80-08-0 ]
[ 2050-48-8 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1987,vol. 96,p. 41 - 50

17
[ 80-08-0 ]
[ 6461-30-9 ]
4,4'-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidinyl-5-sulfonylamido)diphenylsulfone [ No CAS ]
p,p'-(2,4-dioxo-6-methyl-1,2,3,4-tetrahydropyrimidyl-5-sulfonamido)diphenylsulfone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.5 kg	With triethylamine In acetonitrile for 45h; Heating;

Reference： [1]Shirshov; Muslinkin; Reznik; Pashkurov [Pharmaceutical Chemistry Journal, 2000, vol. 34, # 3, p. 132 - 134]

18
[ 28768-32-3 ]
[ 13676-54-5 ]
[ 80-08-0 ]
polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone; 4,4\-bis(maleimido)diphenylmethane [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 3210 - 3221

19
[ 28768-32-3 ]
[ 80-08-0 ]
polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane; dapsone at 140℃; for 16h; Stage #2: at 200℃; for 4h;

Reference： [1]Musto, Pellegrino [Macromolecules, 2003, vol. 36, # 9, p. 3210 - 3221]

20
[ 130-13-2 ]
[ 80-08-0 ]
bis-(4-(1-amino-4-sulfo-2-naphthylazo)phenyl)sulfone disodium salt [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2003,vol. 38,p. 567 - 579

21
[ 80-08-0 ]
[ 32449-92-6 ]
(2S,3S,4R,5S)-6-[(Z)-4-(4-Amino-benzenesulfonyl)-phenylimino]-2,3,4,5-tetrahydroxy-hexanoic acid [ No CAS ]
(2S,3S,4R,5S)-6-((Z)-4-{4-[(2S,3R,4S,5S)-5-Carboxy-2,3,4,5-tetrahydroxy-pent-(Z)-ylideneamino]-benzenesulfonyl}-phenylimino)-2,3,4,5-tetrahydroxy-hexanoic acid [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,2003,vol. 73,p. 1448 - 1452

22
[ 98-01-1 ]
[ 74228-33-4 ]
[ 80-08-0 ]
C₄₀H₃₂N₆O₈S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In methanol Heating;

Reference： [1]Ali, Mohamed Ashraf; Shaharyar, Mohammad [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3314 - 3316]

23
[ 74228-33-4 ]
[ 100-52-7 ]
[ 80-08-0 ]
C₄₄H₃₆N₆O₆S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In methanol Heating;

Reference： [1]Ali, Mohamed Ashraf; Shaharyar, Mohammad [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 12, p. 3314 - 3316]

24
[ 2460-58-4 ]
[ 80-08-0 ]
N,N'-bis(4-nitrosalicylidene)-4,4'-diaminodiphenylsulphone [ No CAS ]

Reference： [1]Heteroatom Chemistry,2008,vol. 19,p. 43 - 47

25
[ 139-65-1 ]
[ 80-08-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dihydrogen peroxide; In water; acetonitrile; at 50℃; for 3h;	General procedure: A solution of sulfide (1 mmol) and catalyst (100 mg), in acetonitrile (9 mL), was added to H2O2 35% (w/v) (10 mmol). The mixture was stirred at 50 C for a time period (see Tables 1 and 2). The solvent was evaporated and then H2O (5 mL) was added. The substrate was extracted with toluene (2 × mL) and dried with anhydrous Na2SO4; filtration and evaporation afforded the corresponding sulfoxides. The crude solids were purified by recrystallization to affordthe pure sulfones
	With dihydrogen peroxide; In acetonitrile; at 25℃; for 24h;	General procedure: Diphenyl sulfide was used as the model reagent for sulfide oxidationstudies. They were performed with H2O2 (aq. solution) as the oxidant,acetonitrile as the solvent, in a batch reactor at 25 C, using POTV (PVWand PV2W) and synthesized hybrid materials (PAACA-PVWX andPAACA-PV2WX) as homogeneous or heterogeneous catalysts respectively. We made experiments using excess of H2O2 (10 mmol ofH2O2 per 1 mmol of sulfide). We also tested the oxidation reaction usinglower amount of oxidant (0.3 and 0.5 ml of 35% w/v H2O2) but verylong reaction times were required to obtain suitable conversion values.So we decided to use 1 ml of 35% w/v H2O2 for the catalytic test. More details about the experimental conditions and the identification of theproducts were added in the supplementary information.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2015,vol. 403,p. 27 - 36
[2]Journal of the American Chemical Society,1938,vol. 61,p. 2763
[3]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 147
[4]Zhurnal Prikladnoi Khimii,1946,vol. 19,p. 580,583, 584
    Chem.Abstr.,1947,p. 2703
[5]Journal of the American Chemical Society,1940,vol. 62,p. 3521
[6]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 68,71
    Chem.Abstr.,1948,p. 723
[7]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 68,71
    Chem.Abstr.,1948,p. 723
[8]Molecular catalysis,2018,vol. 457,p. 8 - 16
[9]Chinese Chemical Letters,2019

26
[ 101-59-7 ]
[ 80-08-0 ]

Yield	Reaction Conditions	Operation in experiment
82%		Example 6: preparation of Dapsone; In a hydrogenation vessel 4-(4'-Nitro-benzenesulfonyl)-phenylmanine (100 g), p-toluensulfonic acid (68.4 g), methanol (350 ml), water (150 ml) and 10% palladium on charcoal (7.6 g) are charge. The mixture is allowed to react with hydrogen at approximately 50C and 5 bar pressure. At reaction completion, hydrochloric acid is added, the catalyst is filtered and dried. 82 g of crude Dapsone are obtained (82% yield; >99.5% purity).
80%		Example 5: preparation of Dapsone; Charge an hydrogenation vessel with 4-(4'-nitro-benzenesulfonyl)-phenylmanine(380g;1.36 mole), water (220 ml), methanol (910 ml) and methansulfonic acid (187kg; 1.95 mole). Then charge under nitrogen, 5% palladium on charcoal (14.4g;0.0067 mole). After inertization, the mixture is added with hydrogen under vigorousstirring up to 4 bar and then heated to 50C. The mixture is maintained under theabove conditions for the least 4 hours. After reaction completion the reactor ispurged with nitrogen several times and the catalyst filtered off. The filter is washedwith methanol (25 ml) and water (200 ml) and the solution is concentrated undervacuum below 50C to remove the organic solvent. A the end, then the mixture isneutralised with 15% ammonia at 50C, then cooled and the product isolated byfiltration.After drying, 315 g of crude product is obtained . Product is crystallised from iso-propanol (1000 ml) and water (700 ml) to give 302 g of pure product (80% yield;>90% purity).

Reference： [1]Patent: WO2006/2690,2006,A1 .Location in patent: Page/Page column 9
[2]Patent: WO2006/2690,2006,A1 .Location in patent: Page/Page column 8
[3]Journal of the American Chemical Society,1938,vol. 61,p. 2763
[4]Zhurnal Prikladnoi Khimii,1946,vol. 19,p. 580,583, 584
Chem.Abstr.,1947,p. 2703

27
[ 1774-36-3 ]
[ 80-08-0 ]

Reference： [1]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132
[2]Journal of the Chinese Chemical Society (Peking),1947,vol. 15,p. 129,132

28
bismethoxyethyl ether [ No CAS ]
[ 79-04-9 ]
[ 80-08-0 ]
[ 17328-16-4 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane	7 4'4"'-Sulfonybis(2-methylaminoacetanilide) EXAMPLE 7 4'4"'-Sulfonybis(2-methylaminoacetanilide) To a stirred solution of 24.83 g of bis(p-aminophenyl)sulfone in 100 ml of dioxane and 200 ml of dimethoxyethyl ether at 50° C. was added a 1:1 mixture of chloroacetyl chloride and dimethoxyenthyl ether. The mixture was heated at 90° C. for 3.5 hours and then allowed to stand at ambient temperature. The solid was collected and crystallized giving 10.2 g of bis[(p-chloroacetamido)phenyl]sulfone.

Reference： [1]Current Patent Assignee: PFIZER INC - US4532349, 1985, A

29
[ 117-21-5 ]
[ 80-08-0 ]
[ 332403-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	Sodium phenylphosphinate; In 1,2-dichloro-benzene; at 180 - 230℃; for 7h;Product distribution / selectivity;	Comparative Example-2; Imidization in Parr Reactor with Up-Front CLPA Addition; A 450 ml Parr pressure-rated reactor equipped as in Comparative Example-1 with two side quartz windows and a partial condenser was charged with solid <strong>[117-21-5]3-chlorophthalic anhydride</strong> (3-ClPA, 21.578 g; 118.2 mmol), phthalic anhydride (0.2664 g; 1.8 mmol), DDS (14.898 g; 60 mmol), sodium phenylphosphinate (50 mg; 0.3 mmol) and o-DCB (85 ml). The reactor was sealed and the temperature was gradually raised. At about 180 C. the reaction mixture was observed to become homogeneous. As water of imidization was removed via the partial condenser the reaction gradually became heterogeneous and eventually the mixture became so thick that mixing of the solid adhering to the quartz window ceased to occur. As the temperature of the reaction mixture was raised further to about 190 C. the heterogeneous reaction mixture began to thin and the viscosity of the heterogeneous mixture was visibly diminished by the time the reaction mixture reached 200 C. Between about 210 C. and about 215 C. most of the solid material present in the reaction mixture dissolved. Thereafter the temperature was raised to 230 C. After about 7 hours imidization was deemed to be complete. Heating was discontinued and as the temperature decreased to about 215 C. the product bisimide began to precipitate from solution. When the temperature had decreased to about 200 C. the product mixture became so thick that efficient stirring could no longer be effected. This Comparative Example illustrates the limitations of “up-front” addition of all of the reactants. Thus, when each of the reactants is added to the reaction vessel at ambient temperature and thereafter the temperature of the reaction mixture is raised. While the reaction mixture is initially homogenous at about 180 C., as water of imidization is removed, the reaction mixture exhibits thick phase behavior which persists until the temperature reaches a higher threshold temperature, in this Comparative Example about 215 C., at which the reaction mixture becomes homogeneous again. The thick phase behavior is undesirable in that it prevents the efficient mixing of the reaction mixture while the thick phase persists and makes accurate measurement of reaction stoichiometry difficult.; Example-1; Imidization in Parr Reactor with Melt CLPA Addition-Procedure:; A 450 ml Parr pressure-rated reactor equipped as in Comparative Example-1 was charged with DDS (14.898 g; 60 mmol), sodium phenylphosphinate (50 mg, 0.3 mmole) and o-DCB (85 mL). The temperature was gradually raised to about 225-230 C. The resultant homogeneous solution was maintained at about 230 C. for 1 hr after which time molten <strong>[117-21-5]3-chlorophthalic anhydride</strong> (3-ClPA, 21.578 g, 118.2 mmole) and phthalic anhydride (0.2664 g; 1.8 mmol) at about 130 C. was added from a stainless steel bomb mounted on top of the reactor. The addition of 3-ClPA was carried out over a period of about 30 to 40 minutes. Water of imidization was azeotropically removed from the reactor via the partial condenser. Throughout the 3-ClPA/PA addition, and thereafter, the reaction mixture was observed to remain a homogeneous solution while at 230 C. No thick phase behavior was observed during the reaction. As the reactor was cooled, the product bisimide was observed to precipitate over a temperature range from about 215 to about 210 C. The reactor was vented when the temperature had decreased to about 170 C. and a sample of the pasty product mixture was withdrawn and analyzed by HPLC. The quality of the product bisimide (“ClPAMI”) was found to be equivalent to the quality of ClPAMI made using known methods.Larger scale imidization reactions using the method of the present invention were conducted in a 5 gallon reactor. The larger reactor was equipped with sampling features which allowed the withdrawal of samples of the reaction mixture as a homogeneous solution without venting the reactor or causing the product bisimide to precipitate during sampling. Examples 2 and 3 are illustrative.A reactor system 10 utilized in various embodiments of the invention is shown in FIG. 1. The reactor system comprised a 5-gallon stainless steel reactor 12 connected directly to monomer and catalyst feed lines 14 and inert gas purge line 15, and indirectly to feed lines 16 for addition of molten reactants. The reactor 12 was connected via distillation line 17 to a partial reflux condenser 18, a total condenser 20 and a back-pressure regulator 22. Feed lines 14 were employed for the batchwise addition of DDS, SSP catalyst, and optionally a portion of the ClPA, whereas, monomer feed lines 16 served for the semi-batch mode introduction of a molten mixture of ClPA and the chain stopper phthalic anhydride (PA). Solvent could be introduced into the reactor via solvent feed line 23.Reactant DDS, ODCB solvent and SPP catalyst were charged to the reactor 12 in batch mode, i.e. prior to starting the reaction. In some reactions a portion of th...
	Sodium phenylphosphinate; In 1,2-dichloro-benzene; at 184.1 - 230.7℃; for 0.05 - 2.41667h;Product distribution / selectivity;	Example 2; The 5-gallon reactor described above and shown in FIG. 1 was equipped with 2 flights of 4-blade pitched turbines, and was charged according to Table I below. TABLE I Component Mass (g) Moles Source 4,4 Diamino Diphenyl Sulfone 1520.8 6.125 Atul (DDS) Phthalic Anhydride (PA) 27.19 0.184 Aldrich Sodium Phenyl Phosphinate 5.0 0.030 Akzo (SPP) 3-Chloro Phthalic Anhydride 2202.8 12.066 Pressure Chem. (ClPA) 1,2 Dicholoro Benzene (ODCB) 9756 66.37 PPG Grade F The reactor was purged with inert gas at 100 SCCM, and the agitation rate was set to 200 rpm. The partial condenser was heated by means of an oil jacket to a temperature of about 130 C. The reactor was heated by setting the reactor oil jacket temperature to 200 C. After 30-minutes of heating, the reactor oil jacket temperature was increased to 230 C. The reactor internal temperature reached a temperature of about 177 C. Water and ODCB were collected as condensed distillate. The reactor pressure was 26.3 psig. Amounts of distillate collected of the course of the reaction, reactor temperature and pressure are shown-in Table II. TABLE II Reactor P Time (min) Reactor T ( C.) (PSIG)H2O (ml) ODCB (ml) 3 184.1 26.3 36 25 6 190.4 26.3 86 52 8 197.4 26.0 114 76 10 205.9 26.4 132 92 16 219.2 25.0 171 117 22 223.5 26.4 186 128 26 225.6 26.4 191 134 30 226.7 26.3 194 138 35 227.7 26.3 198 140 57 230.7 26.2 207 145 After about 1.4 hrs of distillation, the reaction mixture was sampled via the heated sampling port. HPLC analysis of the homogeneous sample indicated that additional 3-ClPA (6.1 grams) was needed to adjust the stoichiometry to within the specified limits. At 2.5 hours of distillation, the 6.1 grams of 3-ClPA was added as a solution of about 9.8 wt % in ODCB.After a total of 4.5 hours the reaction mixture was again sampled. Sample analysis by HPLC indicated that ratio of anhydride to amine was in the range required, from about 1.00 to about 1.03. Therefore, there was no need for any further stoichiometry correction. Heating was continued for a total 9.5 hours at a reactor oil jacket set temperature of 230 C. The reaction was then cooled and diluted with ODCB to provide a slurry of the product so that approximately 3500 grams of solids was obtained as a slurry in 17.8 Kg of ODCB.; Example 3; Melt 3-CLPA Semi-Batch Reaction Mode; The 5-gallon reactor described above and shown in FIG. 1 was equipped with 2 flights of 4-blade pitched turbines, and was charged according to Table III below. TABLE III Component Mass (g) Moles Source 4,4 Diamino Diphenyl Sulfone 1520.8 6.125 Atul Inc. (DDS) Sodium Phenyl Phosphinate 5.0 0.030 Akzo Inc. (SPP) 1,2-Dicholoro Benzene 9991 68.0 PPG Grade F (ODCB) Heated tank 24 (FIG. 1) was charged with phthalic anhydride (PA) and <strong>[117-21-5]3-chlorophthalic anhydride</strong> (3-ClP) in the amounts shown in Table IV and heated to 140 C. in order to melt the 3-ClPA/PA solids. ODCB (240 grams) was then added to the molten mixture of 3-ClPA and PA which was completely miscible with the ODCB. Thus, the mixture in heated tank 24 comprised 3-ClPA (89.2 wt %), ODCB (9.7 wt %), and PA (1.1 wt %). The small amount of ODCB solvent employed helped to facilitate complete transfer of the anhydride reactants into the reaction mixture. TABLE IV Component Mass (g) Moles Source Phthalic Anhydride 27.20 0.184 Aldrich 3-Chlorophthalic Anhydride 2203.0 12.067 Pressure Chem. 1,2-Dicholorobenzene 240.0 1.63 PPG Grade F The 5-gallon reactor was purged with inert gas at 100 SCCM, and the agitation rate was set to 200 rpm. The partial condenser was heated by means of an oil jacket to a temperature of 130 C. The reactor was heated commenced by setting the reactor oil jacket temperature to 180 C. After 30-minutes, the oil jacket temperature was increased to 225 C. At the 1.0-hour mark, the reactor reached a temperature of 226 C., at which point the melt addition of the 3-ClPA-PA-ODCB melt mixture from heated tank 24 was commenced. The reactor pressure was 25.1 PSIG. The 3-ClPA-PA-ODCB melt mixture was pumped via melt feed pump 26 and melt feed line 27 into reactor 12 at an average rate of about 21.5 grams/minute. Addition of the 3-ClPA at a temperature in excess of 210 C. avoided the thick phase reaction stage observed when the reactants are brought into contact at temperatures below about 190 C.About 15 minutes after the addition of the 3-ClPA-PA-ODCB melt mixture was initiated, water and ODCB distillate were observed in the overheads from the partial reflux condenser 18. Addition of the 3-ClPA-PA-ODCB melt mixture required about 2 hours to complete. During the addition of the 3-ClPA-PA-ODCB melt mixture, the amounts of water and ODCB condensed from the overheads emerging from the partial reflux condenser were recorded as a function of time and are recorded in Table V, along with the reactor temperature and pressure profiles. TABLE V Reactor P Time (min)* Reactor T ( C.) (PSIG)H2O (ml) ODCB (ml) 10 222.4 26.5 23 20 20 223.1 26.4 42 33 25 223.2 26.4 53 39 30 223.3 26.5 63 46...

Reference： [1]Patent: US2008/119660,2008,A1 .Location in patent: Page/Page column 8-9
[2]Patent: US2008/119660,2008,A1 .Location in patent: Page/Page column 9-10

30
[ 4619-20-9 ]
[ 80-08-0 ]
N'-(4-{4-[3-(4-methylphenyl)-3-oxopropylcarboxamido]phenylsulfonyl}phenyl)-4-(4-methylphenyl)-4-oxobutanamide [ No CAS ]

Reference： [1]Journal of the Chilean Chemical Society,2010,vol. 55,p. 74 - 77

31
[ 32707-89-4 ]
[ 80-08-0 ]
[ 1370557-72-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 847 - 862

32
[ 90-02-8 ]
[ 80-08-0 ]
[ 7251-84-5 ]

Yield	Reaction Conditions	Operation in experiment
97.1%	With toluene-4-sulfonic acid; In chloroform; for 8h;Inert atmosphere; Reflux;	S1, the synthesis of intermediates: 1 mol of 4,4'-diaminophenylsulfone and 200 ml of trichloromethane were mixed, Under nitrogen protection, the temperature was raised to the reflux temperature of chloroform, Then 2.5 mol of 2-hydroxybenzaldehyde and 0.1 g of p-toluenesulfonic acid were added and reacted for 8 hours. After the end of the reaction, the mixture was filtered and washed with trichloromethane three times and dried to obtain 0.97 mol of orange-red intermediate, The yield of the intermediate was 97.1%

Reference： [1]Patent: CN107098937,2017,A .Location in patent: Paragraph 0056
[2]E-Journal of Chemistry,2011,vol. 8,p. 1218 - 1225

33
[ 708-06-5 ]
[ 80-08-0 ]
[ 21708-77-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	In methanol; at 20℃; for 1.5h;	General procedure: All the tetra dentate Schiff base ligands were prepared by condensation between diamines and 2-hydroxy-1-naphthaldehyde in methanol and purified by recrystallization from a methanol through the partial evaporation ofthe more volatile dichloromethane. Schiff base ligands prepared by dissolving 2-hydroxy-1-naphthaldehyde (0.5 g, 2.9 mmol) and diamine (0.15 g, 1.45 mmol) in methanol with stirring inone portion. The stirring was continued to completion of the reaction. The progress of the reaction was monitored by thin layer chromatography (TLC). After the completion of the reaction, a colored substance was obtained. The solid product was filtered and washed with cold MeOH. The crude product was purified by recrystallization from methanol and the pure Schiff base was obtained in high yield after leaving for the appropriate time. The Schiff bases were characterized by physical and spectroscopic data [15].
	In methanol;	General procedure: All tetradentate Schiff bases were prepared by the condensation of diamines (1 mmol) with 2-hydroxy-1-naphtaldehyde (2 mmol) in methanol under stirring. After the completion of the reaction (TLC monitoring), the obtained colored substances were collected by filtration and washed with cold MeOH. The crude products were purified by recrystallization from ethanol. The physical and spectroscopic data for the synthesized Schiff bases were in good agreement with the published data.

Reference： [1]Bulletin of the Chemical Society of Ethiopia,2013,vol. 27,p. 143 - 149
[2]Russian Chemical Bulletin,2015,vol. 64,p. 1814 - 1818
Izv. Akad. Nauk, Ser. Khim.,2015,p. 1814 - 1818,5

34
[ 104-88-1 ]
[ 762-04-9 ]
[ 80-08-0 ]
[ 1448137-80-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With CeCl3·7H2O-SiO2; In neat liquid; for 0.0666667h;Microwave irradiation;	General procedure: The mixture of Dapsone (3) (1 mmol, 248 mg), 3-nitrobenzaldehyde (4c) (1.1 mmol, 167 mg), diethylphosphite (5) and the catalyst, CeCl3·7H2O-SiO2 (12 mol%) was placed into a 50 mL flat-bottomed flask. The reaction mixture was irradiated under microwave radiations using catalyst systems (CATA-4R), % power is 65% and 465 W. After completion of the reaction (monitored by TLC), DCM (15 mL) was added to the reaction mixture. The catalyst was filtered and washed with DCM (5 mL) to recover it. The combined filtrates and washings were concentrated under reduced pressure, followed by purification on column chromatography using ethylacetate:n-hexane in the ratio of 4:6 as an eluent to afford pure tetraethyl[4,4'-sulfonylbis(4,1-phenylene)bis(azanediyl)]bis[(3-nitrophenyl)methylene]diphosphonate (6c). The filtered residue catalyst was dried under vacuum and reused for the next reaction. This same procedure was adopted for preparing the remaining title products.

Reference： [1]Chinese Chemical Letters,2013,vol. 24,p. 759 - 763

35
[ 3132-99-8 ]
[ 762-04-9 ]
[ 80-08-0 ]
[ 1448137-81-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With CeCl3·7H2O-SiO2; In neat liquid; for 0.0666667h;Microwave irradiation;	General procedure: The mixture of Dapsone (3) (1 mmol, 248 mg), 3-nitrobenzaldehyde (4c) (1.1 mmol, 167 mg), diethylphosphite (5) and the catalyst, CeCl3·7H2O-SiO2 (12 mol%) was placed into a 50 mL flat-bottomed flask. The reaction mixture was irradiated under microwave radiations using catalyst systems (CATA-4R), % power is 65% and 465 W. After completion of the reaction (monitored by TLC), DCM (15 mL) was added to the reaction mixture. The catalyst was filtered and washed with DCM (5 mL) to recover it. The combined filtrates and washings were concentrated under reduced pressure, followed by purification on column chromatography using ethylacetate:n-hexane in the ratio of 4:6 as an eluent to afford pure tetraethyl[4,4'-sulfonylbis(4,1-phenylene)bis(azanediyl)]bis[(3-nitrophenyl)methylene]diphosphonate (6c). The filtered residue catalyst was dried under vacuum and reused for the next reaction. This same procedure was adopted for preparing the remaining title products.

Reference： [1]Chinese Chemical Letters,2013,vol. 24,p. 759 - 763

36
[ 98-03-3 ]
[ 762-04-9 ]
[ 80-08-0 ]
[ 1448137-83-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With CeCl3·7H2O-SiO2; In neat liquid; for 0.0833333h;Microwave irradiation;	General procedure: The mixture of Dapsone (3) (1 mmol, 248 mg), 3-nitrobenzaldehyde (4c) (1.1 mmol, 167 mg), diethylphosphite (5) and the catalyst, CeCl3·7H2O-SiO2 (12 mol%) was placed into a 50 mL flat-bottomed flask. The reaction mixture was irradiated under microwave radiations using catalyst systems (CATA-4R), % power is 65% and 465 W. After completion of the reaction (monitored by TLC), DCM (15 mL) was added to the reaction mixture. The catalyst was filtered and washed with DCM (5 mL) to recover it. The combined filtrates and washings were concentrated under reduced pressure, followed by purification on column chromatography using ethylacetate:n-hexane in the ratio of 4:6 as an eluent to afford pure tetraethyl[4,4'-sulfonylbis(4,1-phenylene)bis(azanediyl)]bis[(3-nitrophenyl)methylene]diphosphonate (6c). The filtered residue catalyst was dried under vacuum and reused for the next reaction. This same procedure was adopted for preparing the remaining title products.

Reference： [1]Chinese Chemical Letters,2013,vol. 24,p. 759 - 763

37
[ 28768-32-3 ]
[ 80-08-0 ]
[ 103443-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	Heating;

Reference： [1]Okabe, Tomonaga; Takehara, Tomohiro; Inose, Keisuke; Hirano, Noriyuki; Nishikawa, Masaaki; Uehara, Takuya [Polymer, 2013, vol. 54, # 17, p. 4660 - 4668]

38
[ 28768-32-3 ]
[ 80-08-0 ]
C₆₂H₇₂N₆O₁₀S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Heating 2: Heating

Reference： [1]Okabe, Tomonaga; Takehara, Tomohiro; Inose, Keisuke; Hirano, Noriyuki; Nishikawa, Masaaki; Uehara, Takuya [Polymer, 2013, vol. 54, # 17, p. 4660 - 4668]

39
[ 621-59-0 ]
[ 67-52-7 ]
[ 80-08-0 ]
[ 1465917-65-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With phosphotungstic acid; In ethanol; at 80℃; for 12h;Green chemistry;	General procedure: A mixture of barbituric acid (0.26 g, 2 mmol), aldehyde(1 mmol), amine (1 mmol), and H3PW12O40 (0.04 g, 2 mol %) inethanol (5 mL) at 80 C was stirred for 12 h. As completion ofthe reaction confirmed by TLC (eluent EtOAc/MeOH), thereaction mixture was cooled to room temperature. Then, theprecipitated product was filtered and washed withwater (2 10 mL) and ethanol (2 5 mL) to afford the pureproduct.4.1.7 9-[4-(4-Amino-benzenesulfonyl)-phenyl]-10-(3-hydroxy-4-methoxy-phenyl)-9,10-dihydro-1H,8H-1,3,6,8,9-pentaaza-anthracene-2,4,5,7-tetraone (L5) Yield: 83%; yellow solid; mp >350 C. IR (KBr): 3374, 3115, 1693, 1677, 935, 807 cm-1. 1H NMR (250 MHz, DMSO-d6/TMS): delta = 3.86 (s, 3H, OCH3), 4.82 (s, 1H, CH), 6.68 (s, 1H, Ar), 6.85 (d, J = 9.5 Hz, 2H, Ar), 7.02 (d, J = 9.2 Hz, 4H, Ar), 7.83 (d, J = 9.5 Hz, 4H, Ar), 9.43 (br s, 1H, OH), 11.12 (s, 2H, NH), 11.25 (s, 2H, NH). 13C NMR (62.9 MHz, DMSO-d6/TMS): delta = 27.1, 57.0, 80.4, 115.8, 116.8, 118.1, 123.5, 127.9, 129.2, 132.1, 143.5, 146.9, 151.8, 152.5, 166.3. MS: 602.11 (8.9%, M+). Anal. Calcd for C28H22N6O8S (602.57): C, 55.81; H, 3.68; N, 13.95. Found: C, 55.93; H, 3.73; N, 14.06.

Reference： [1]Carbohydrate Research,2013,vol. 380,p. 81 - 91

40
[ 75-77-4 ]
[ 80-08-0 ]
4,4'-bis(N,N'-trimethylsilyl)amine diphenylsulfone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine; In tetrahydrofuran; at 20 - 45℃; for 16h;Inert atmosphere;	DDS (1.24 g, 5 mmol) was dissolved in THF/Et3N (40/10 mL) mixed solvent at room temperature. Trimethylchlorosilane (2.17 g, 20 mmol) was then added dropwise into the solution. After completion of dropping, the reaction mixture was further stirred for 16 h at 45 C. Then the mixture was filtered and concentrated under reduced pressure. To further purify the product, the resulting orange powder was dissolved in THF (20 mL) and filtered. All volatiles were removed under reduced pressure. 1.79 g compound 1 was obtained in 91% yield as a gray white powder.
91%	With pyridine; In acetone; at 40℃; for 0.5h;Inert atmosphere;	Example 1Preparation of 4,4'-bis(N,N'-trimethylsilyl)aminodiphenyl sulfoneUnder nitrogen atmosphere, to two-necked flask were successively added 4,4'-diaminodiphenylsulfone(1. 24g, 5mmol), acetone (20 mL) and pyridine (20 mL), stirred to dissolve, warmed to 40 C, the trimethylchlorosilane(1. 09g, lOmmol) was added dropwise After into the solution, after the addition was complete the reaction solution to amine 0.5 hours, cooled to room temperature, filtered, and the solvent was removed under reduced pressure50 C and dried in vacuo to give a pale yellow solid, yield 91%,

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 749,p. 251 - 254
[2]Patent: CN103408577,2016,B .Location in patent: Paragraph 0061; 0062; 0063; 0064; 0065; 0066; 0067

41
[ 1719-58-0 ]
[ 80-08-0 ]
4,4'-bis(N,N'-dimethylvinylsilyl)amine diphenylsulfone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In tetrahydrofuran; at 20 - 45℃; for 16h;Inert atmosphere;	General procedure: DDS (1.24 g, 5 mmol) was dissolved in THF/Et3N (40/10 mL) mixed solvent at room temperature. Trimethylchlorosilane (2.17 g, 20 mmol) was then added dropwise into the solution. After completion of dropping, the reaction mixture was further stirred for 16 h at 45 C. Then the mixture was filtered and concentrated under reduced pressure. To further purify the product, the resulting orange powder was dissolved in THF (20 mL) and filtered. All volatiles were removed under reduced pressure. 1.79 g compound 1 was obtained in 91% yield as a gray white powder.
92%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere;	Example 2Preparation of 4,4'-bis(N,N'-dimethylvinylsilyl)aminodiphenyl sulfoneUnder nitrogen atmosphere, two-necked flask were successively added 4,4'-diaminodiphenylsulfone(1. 74g, 7mmol),In tetrahydrofuran (30 mL) and diisopropylethylamine amine (20 mL), stirred and dissolved, 20 C, a solution of chloro(dimethyl)vinylsilane(2. llg, 17. 5_1) was added dropwise to the above solution, after the addition was complete amidation reaction for 2 hours, filtered, and solvent was removed under reduced pressure. after the addition was complete amidation reaction for 2 hours, filtered, and solvent was removed under reduced pressureAfter the agent is 50 C and dried in vacuo to give a pale yellow solid, yield 92%,

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 749,p. 251 - 254
[2]Patent: CN103408577,2016,B .Location in patent: Paragraph 0068; 0069; 0070; 0071; 0072; 0073; 0074

42
[ 2050-48-8 ]
[ 80-08-0 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 15037 - 15040

43
[ 117-80-6 ]
[ 80-08-0 ]
[ 20013-15-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	In water; for 2h;Reflux;	A mixture of 2,3-dichloro-1,4-naphthoquinone (2.270 g,10 mmol) and 4-aminophenyl sulfone (2.048 g, 10 mmol) wasadded to distilled water (800 mL) and refluxed for 2 h. The reactionmixture was cool to room temperature. The red precipitate formed,separated by filtration, washed with hot water (200 mL), dried at80 C, and crystallized from 95% ethyl alcohol to give compound1 (3.850 g, 88%) as red crystals; mp-239.5-240.5 C [18]; IR(KBr): 1259, 1317, 1516, 1585, 1627, 1676, 1699, 2312, 3286,3707 cm1; 1H NMR (500 MHz, DMSO-d6) d: 6.12 (s, 2H), 6.60 (d,2H, J = 5.2 Hz), 7.17 (d, 2H, J = 4.8 Hz), 7.52 (d, 2H, J = 6.8 Hz),7.70 (d, 2H, J = 6.8 Hz), 7.80 (t, 1H, J = 7.2 Hz), 7.85 (t, 1H,J = 7.0 Hz), 8.02 (t, 2H, J = 8.0 Hz), 9.50 (s, 1H); 13C NMR(125 MHz, DMSO-d6) d: 112.9, 119.0, 122.1, 125.9, 126.1, 126.5,126.6, 129.1, 130.4, 131.6, 133.4, 134.6, 137.0, 142.5, 143.1,153.3, 176.9, 179.7; HRMS (EI) m/z: Calcd for C22H15ClN2O4S:438.8835 found: 438.8832.

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 139,p. 477 - 487
[2]ChemMedChem,2019,vol. 14,p. 532 - 544
[3]ChemistryOpen,2019,vol. 8,p. 589 - 600
[4]Dyes and Pigments,2020,vol. 172
[5]Analytical Chemistry,2019,vol. 91,p. 10095 - 10101

44
[ 353-50-4 ]
[ 80-08-0 ]
C₁₄H₁₀F₂N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In acetone; at 20℃; for 3h;Glovebox;	A vigorously stirring solution of BSDA (5 mmol), anhydrous acetone (15 g), and m-dichlorobenzene (15 g) were added into a polyfluoroalkoxy(PTA) cylindrical reactor. COF2 was induced to the mixture with the flow amount of 12 ml/min for 3 h at room temperature. COF2 and HF left in the reactor and pipeline were removed by nitrogen gas, and white intermediate 15 (100% yield) with the structure of N-fluoroformyl was gained. After heating the mixture under reflux temperature 171C with a nitrogen gas stream for 3 h, isocyanate 16 was obtained (97% yield) as a yellow solid after evaporating solvent under reduced pressure. The colorless needle crystal was gained by the recrystallization in toluene.
	In acetone; at 20℃; for 3h;	The 298g (1.2 muM) 4, 4' - sulfonyl diphenyl diamine (BSDA) and 300 ml acetone, 300 ml of dichlorobenzene to join with mixer 1.50L stainless steel reactor, filled with 396g (6.0 muM) after the carbonyl of the closed system, reacting at room temperature 3h after, to reactor as rectification, direct rectification, regulating the sump temperature, to ensure that the system pressure is 1 mpa, tower-top temperature is -40 C, carbonyl fluoride extracted 219g, recovery is 92.3%, then the sump heating up to 100 C the left and right, to ensure that the system pressure is 0.6 mpa, tower-top temperature is 20 C, is extracted hydrogen fluoride 42g, recovery is 87.5%. Then in normal pressure, temperature 140 C lower reaction 2h removing hydrogen fluoride, after the reaction is completed, the top of the coolant temperature is 20 C, extracted hydrogen fluoride 40g, recovery is 83.3%, the system after cooling down to room temperature, filter to get a yellow solid 4, 4' - sulfonyl diphenyl diisocyanate (BSDI) crude 364g, purity of 96.0%, the product yield 97.1%. Recovery of the solvent the crude product after the water washing, alkali cleaning, distillation 290 ml acetone and 287 ml dichlorobenzene, to return to the solvent storage tank

Reference： [1]Journal of Fluorine Chemistry,2015,vol. 176,p. 26 - 30
[2]Patent: CN106631899,2017,A .Location in patent: Paragraph 0071-0072

45
[ 1376771-60-6 ]
[ 80-08-0 ]
3,3'-[sulfonyldi(4,1-phenylene)]bis(1,5,3-dithiazepane) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%		General procedure: A mixture of 0.272 g(2 mmol) of 1,3,6-oxadithiepane (1) and 0.022 g (0.05 mmol) of Sm(NO3)3 · 6H2O in 10 mL of chloroform was stirred for 30 min at room temperature under argon, 1 mmol of the corresponding diamine in 10 mL of ethanol was added, and the mixture was stirred for 3 h at room temperature. The mixture was then treated with 2 mL of water, stirred for 30 min, and extracted with chloroform (20 mL). The extract was evaporated,and the residue was subjected to column chromatographyon silica gel. Compound 4 was isolated as colorless oily material, and compounds 2, 3, and 5-8 were colorless crystals (recrystallized from CHCl3).

Reference： [1]Russian Journal of Organic Chemistry,2015,vol. 51,p. 1788 - 1792
Zh. Org. Khim.,2015,vol. 51,p. p1821 - p1825,5

46
[ 28900-10-9 ]
[ 80-08-0 ]
2-(4-aminophenylsulfonyl)phenylamino-6-methylnicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine; In N,N-dimethyl-formamide; for 24h;Reflux;	A mixture of (II) (1.52 g, 0.01 mol) anddapsone (2.48 g, 0.01 mol) in dry dimethylformamide(10 mL) containing 3 drops of trimethylamine was refluxed for 24 h. The obtained solid while hot was recrystallized from dioxane to give (XXI). Yield 63%; mp139.3C. IR: 3401, 3361 (NH, NH2), 3079 (CHarom.), 2971, 2836 (CH aliph.), 2228 (C?N), 1618(C=N), 1377, 1154 (SO2). 1H NMR: 2.3 (s, 3H,CH3), 6.6 (s, 2H, NH2, exchangeable with D2O), 6.9-8.2 (m, 10H, ArH), 11.0 (s, 1H, NH, exchangeablewith D2O). 13C NMR: 25.1, 112.4, 112.7 (2), 114.4,115.9 (2), 117.0, 128.3 (4), 130.0 (2), 142.4, 144.9,149.2, 153.4, 158.9. MS, m/z (%): 364 (M+) (14.1165), 347 (100). Calcd. for C19H16N4O2S(364.42): C, 62.62; H, 4.43; N, 15.37. Found: C,62.94; H, 4.11; N, 15.07.

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

47
[ 28900-10-9 ]
[ 80-08-0 ]
C₂₆H₂₀N₆O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With triethylamine; In N,N-dimethyl-formamide; for 24h;Reflux;	A mixture of (II)(3.04 g, 0.02 mol) and dapsone (2.48 g, 0.01 mol) indry dimethylformamide (10 mL) containing 3 drops oftrimethylamine was refluxed for 24 h. The obtainedsolid after poured onto ice water was recrystallizedfrom dioxane to give (XXII). Yield 56%; mp 173.9C.IR: 3404, 3171(NH), 3079 (CH arom.), 2966, 2836(CH aliph.), 2226 (C?N), 1622 (C=N), 1377, 1141(SO2). 1H NMR: 2.4 (s, 6H, 2CH3), 6.5-8.6 (m, 12H,ArH), 10.6 (s, 2H, 2NH, exchangeable with D2O).13CNMR: 25.4 (2), 109.6 (2), 112.8 (2), 113.7 (4), 114.0(2), 128.8 (4), 129.3 (2), 139.9 (2), 144.9 (2), 155.5 (2),160.1 (2). MS, m/z (%): 480 (M+) (44.6408), 240 (100).Calcd. for C26H20N6O2S (480.54): C, 64.98; H, 4.20; N,17.49. Found: C, 64.64; H, 4.51; N, 17.87.

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

48
[ 15761-39-4 ]
[ 80-08-0 ]
tert-butyl (S)-2-((4-((4-((S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido)phenyl)sulfonyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;	A mixture of 4,4?-Diaminodiphenyl Sulfone 1 (481mg, 1.94mmol), N-Boc-l-proline (1.00g, 4.65mmol), and EDCI (945mg, 5.03mmol) in CH2Cl2 (10mL) was stirred at room temperature for 16h. The mixture was then poured in 1N aq. HCl solution and extracted with CH2Cl2. The organic layer dried over magnesium sulfate, filtered, and concentrated in vacuo. Then without any purification, tert-Butyl (S)-2-((4-((4-((R)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxamido)phenyl)sulfonyl)phenyl)carbamoyl)pyrrolidine-1-carboxylate 2 was obtained as white solid (544mg, 44%). 1H NMR (DMSO-d6, delta=2.5ppm, 400MHz): 10.43 (s, 2H), 7.89-7.79 (m, 8H), 4.27-4.18 (m, 2H), 3.44-3.39 (m, 4H), 2.19-2.16 (m, 2H), 1.99-1.78 (m, 6H), 1.38-1.23 (app br s, 18H). 13C NMR (DMSO-d6, delta=39.52ppm, 100MHz): 172.3, 153.0, 143.4, 135.3, 128.5, 119.2, 113.0, 78.6, 62.8, 60.4, 46.5, 45.1, 33.1, 30.9, 30.1, 27.9, 26.7, 26.6, 24.0, 23.4, 13.1. HRMS (ESI) m/z: Anal. calcd. for [M+Na]+ C32H42N4NaO8S: 665.2616; found 665.2613.
44%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 16h;	4,4'-diaminodiphenyl sulfone (481 mg, 1.94 mmol), N-Boc-L-proline (1.00 g, 4.65 mmol) And ethyl 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDCI) (945 mg, 5.03 mmol) Was dissolved in dichloromethane (10 mL) The mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with 1 N aqueous hydrochloric acid solution and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, The mixture was concentrated in vacuo to give the desired compound (S) -2 - ((4 - ((R) -1- (tert-butoxycarbonyl) pyrrolidine- 2- carboxamido) phenyl) sulfonyl) phenyl) Carbamoyl) pyrrolidine-1-carboxylate (544 mg, 44% yield) as a white solid.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 87 - 100
[2]Patent: KR2017/31307,2017,A .Location in patent: Paragraph 0177-0179

49
[ 628-36-4 ]
[ 80-08-0 ]
4-(4-(4-(4H-1,2,4-triazol-4-yl)benzenesulfonyl)phenyl)-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	at 150℃; for 24h;	In the presence of a magnet, 4-(4-aminobenzenesulfonyl)aniline (1 mmol) and 1,2-<strong>[628-36-4]diformylhydrazine</strong> (4 mmol) were added to a 50 mL three-neck round bottom flask equipped with a reflux condenser and a thermometer respectively. Start stirring at 150°C for 24 hours. After completion of the reaction, the reaction solution was cooled to room temperature and filtered. The resulting precipitate was added to 100 mL of hot methanol. After stirring and dissolving, filter. The filtrate was slowly evaporated to give a white solid, yield 85percent.
85%	at 150℃; for 24h;	The molar ratio of 4- (4-aminobenzenesulfonyl) aniline: bisformylhydrazide was 1: 4A 50 mL three-necked round-bottomed flask equipped with a magnetron, a reflux condenser and a thermometer was charged with 4- (4-aminobenzenesulfonylYl) aniline (1 mmol) and bisformylhydrazide (4 mmol) were added and the mixture was stirred for 24 hours at 150 ° C. After completion of the reaction,The solution was cooled to room temperature and the resulting precipitate was added to 100 mL of hot methanol. After stirring, the solution was filtered and the filtrate was slowly evaporated to obtain whiteColor solid, yield 85percent.

Reference： [1]Patent: CN105669570,2016,A .Location in patent: Paragraph 0018
[2]Patent: CN105503911,2016,A .Location in patent: Paragraph 0018; 0019

50
[ 600-18-0 ]
[ 104-87-0 ]
[ 80-08-0 ]
6-(4-carboxy-3-methyl-2-p-tolylquinolin-6-ylsulfonyl)-3-methyl-2-p-tolylquinoline-4-carboxylic acid [ No CAS ]