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[ CAS No. 3704-28-7 ] {[proInfo.proName]}

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Chemical Structure| 3704-28-7
Chemical Structure| 3704-28-7
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Product Details of [ 3704-28-7 ]

CAS No. :3704-28-7 MDL No. :MFCD00068039
Formula : C9H10O2S Boiling Point : -
Linear Structure Formula :- InChI Key :CPQDZXPLQXZJGF-UHFFFAOYSA-N
M.W : 182.24 Pubchem ID :279586
Synonyms :

Safety of [ 3704-28-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3704-28-7 ]

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

  • Downstream synthetic route of [ 3704-28-7 ]

[ 3704-28-7 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 3704-28-7 ]
  • [ 885949-42-8 ]
YieldReaction ConditionsOperation in experiment
With hydrazine hydrate
With hydrazine hydrate In ethanol
  • 3
  • [ 4892-02-8 ]
  • [ 74-88-4 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In ethanol
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; 13.A To a solution of methyl thiosalicylate (4.0 g, 23.8 mmol) in DMF (25 mL) is added K2CO3 (4.0 g, 28.94 mmol) followed by methyl iodide (2.3 mL, 36.9 mmol). The resulting mixture is stirred at ambient temperature for 1 h. The mixture is diluted with EtOAc and washed with 1 N HCI (3x) and water (1x). The organic phase is dried over MgSO4, filtered and concentrated to afford 2-methylsulfanylbenzoic acid methyl ester.
  • 4
  • [ 104-92-7 ]
  • [ 3704-28-7 ]
  • [ 75444-97-2 ]
YieldReaction ConditionsOperation in experiment
With magnesium; methyl iodide 1.) THF, reflux, 2 h, 2.) r.t., 1.5 h; Yield given. Multistep reaction;
  • 5
  • [ 3704-28-7 ]
  • [ 29917-03-1 ]
  • S-(2-methoxycarbonylphenyl)S-methyl-N-(4-methoxyphenylsulphonyl)-sulphilimine [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With acetic acid at 40℃; for 0.5h;
  • 6
  • [ 3704-28-7 ]
  • methyl 2-methylsulfinylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With dihydrogen peroxide; 8-chloro-1,10-ethyleneisoalloxazinium chloride In methanol at 25℃; for 24h; chemoselective reaction;
81% With 2-Chlorothioxanthone at 20℃; Irradiation; Sealed tube; General procedure D to the synthesis of sulfoxides General procedure: A solution of sulfides 1 (0.2 mmol, 1.0 equiv), photocatalyst (a, 0.1 mol%), and HFIP (2 mL, 0.1 M) was sealed in an oven-dried reaction tube equipped with an air balloon. The reaction was agitated under 18 W 405 nm (the wave lengthen sees below Fig. 1) LEDs at room temperature for 12 to 24 h. The progress of the reaction was monitored by GC-MS or/and TLC. After the completion of the reaction, the solvent was removed under reduced pressure, and the crude product 2 was purified by flash silica chromatography using n-hexanes and ethyl acetate as eluent (v/v, 50:50).
37% With ammonium hydroxide; sodium hypochlorite; chloroamine; ammonium chloride; acetyl chloride In dichloromethane; water at 0℃; Flow reactor;
With perchloric acid; dihydrogen peroxide In ethanol; water at 25℃; var. solvents;
With lead(IV) acetate In acetic acid at 14.9℃; ΔH(excit.), ΔS(excit.); other temperatures;
With potassium permanganate In water; acetic acid at 24.9℃; mechanism, other temperatures, ΔH(excit.), ΔS(excit.);
With sodium periodate In ethanol; water at 25℃; pH=8;
With tripropylammonium fluorochromate (VI) In N,N-dimethyl-formamide at 4.9℃; ΔH(excit.), ΔS(excit.), var. temperature;
With pyridinium chlorochromate In acetic acid at 30 - 40℃; ΔH(excit.), ΔS(excit.);
With bis(2,2'-bipyridyl) copper(II) permanganate In water; acetic acid at 19.9℃; other temperatures; kinetics and mechanism of the oxidation of organic sulfides by BBCP; formation constants, thermodynamic parameters (ΔH, ΔS, ΔG) and rate of decomposition of sulfide-BBCP complex; substituent effect; effect of acidity;
With pyridinium hydrobromide perbromide; acetic acid at 14.9℃; ΔH(a), ΔS(a);
With trimethylbenzylammonium bromide; acetic acid at 14.9℃; ΔH(activ.), ΔS(activ.); var temp.;
With pyridinium bromochromate In N,N-dimethyl-formamide at 19.9℃; ΔH(excit.), ΔS(excit.); var. temp.;
With lead(IV) acetate In acetic acid for 24h;
2.4 % Chromat. With phosphate buffer; VBrPO from Corallina officinalis; dihydrogen peroxide In propan-1-ol; water at 25℃; other solvent composition, effect of absence of enzyme;
With HMTAB In acetic acid at 14.85℃; for 20h;
With quinolinium monofluorochromate(VI) In N,N-dimethyl-formamide at 19.85 - 49.85℃;
With quinolinium bromochromate In dimethyl sulfoxide at 14.85℃; for 20h;
With morpholinium chlorochromate In dimethyl sulfoxide
With tetraethylammonium chlorochromate(VI) In dimethyl sulfoxide at 44.84℃;
With bis(pyridine)silver(I) permanganate In water; acetic acid at 24.84℃;
With imidazolium fluorochromate In dimethyl sulfoxide at 44.84℃; for 20h;
20 %Chromat. With E104A, F146A, K199A, D202A, S477Z mutant of prolyl oligopeptidase from Pyrococcus furiosus, modified with bicyclo[6,1,0]nonyne-substi-tuted 9-mesityl-10-methylacridinium at Z477, where Z is p-azido-L-phenylalanine In acetonitrile at 20℃; Irradiation; Enzymatic reaction;

Reference: [1]Location in patent: experimental part Marsh, Barrie J.; Carbery, David R. [Tetrahedron Letters, 2010, vol. 51, # 17, p. 2362 - 2365]
[2]Zhao, Bin; Hammond, Gerald B.; Xu, Bo [Tetrahedron Letters, 2021, vol. 82]
[3]Danahy, Kelley E.; Styduhar, Evan D.; Fodness, Aria M.; Heckman, Laurel M.; Jamison, Timothy F. [Organic Letters, 2020, vol. 22, # 21, p. 8392 - 8395]
[4]Ruff, Ferenc; Kucsman, Arpad [Gazzetta Chimica Italiana, 1990, vol. 120, # 4, p. 241 - 246]
[5]Banerji, Kalyan K. [Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 759 - 763]
[6]Banerji, Kalyan K. [Tetrahedron, 1988, vol. 44, # 10, p. 2969 - 2976]
[7]Ruff, Ferenc; Kucsman, Arpad [Journal of the Chemical Society. Perkin transactions II, 1985, p. 683 - 688]
[8]Banerji, Kalyan K. [Journal of the Chemical Society. Perkin transactions II, 1988, p. 2065 - 2070]
[9]Rajasekaran, K.; Baskaran, T.; Gnanasekaran, C. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1987, vol. 26, # 11, p. 956 - 957]
[10]Bohra, Anupama; Sharma, Pradeep K.; Banerji, Kalyan K. [Journal of Organic Chemistry, 1997, vol. 62, # 11, p. 3562 - 3567]
[11]Vijas, Vijaj K.; Jalani, Neeta; Kothari, Seema; Banerji, Kalyan K. [Journal of Chemical Research, Miniprint, 1996, # 8, p. 2201 - 2220]
[12]Goel, Shruti; Varshney, Seema; Kothari, Seema; Banerji, Kalyan K. [Journal of Chemical Research, Miniprint, 1996, # 12, p. 2901 - 2922]
[13]Loonker, Kavita; Sharma, Pradeep K.; Banerji, Kalyan K. [Journal of Chemical Research, Miniprint, 1997, # 6, p. 1262 - 1285]
[14]Banerji, Kalyan K. [Journal of the Chemical Society. Perkin transactions II, 1991, # 5, p. 759 - 763]
[15]Andersson, Malin A.; Allenmark, Stig G. [Tetrahedron, 1998, vol. 54, # 50, p. 15293 - 15304]
[16]Choudhary, Kirti; Suri, Deepa; Kothari, Seema; Banerji, Kalyan K. [Journal of Physical Organic Chemistry, 2000, vol. 13, # 5, p. 283 - 292]
[17]Bhandari, Abhinav; Sharma, Pradeep. K.; Banerji, Kalyan K. [Journal of Chemical Research, Miniprint, 2001, # 6, p. 653 - 675]
[18]Dhariwal, Varsha; Yajurvedi, Deeksha; Sharma, Pradeep K. [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2006, vol. 45, # 5, p. 1158 - 1164]
[19]Location in patent: experimental part Malani, Neha; Baghmar, Manju; Sharma, Pradeep K. [International Journal of Chemical Kinetics, 2009, vol. 41, # 1, p. 65 - 72]
[20]Location in patent: experimental part Sharma, Deepika; Pancharia; Vadera; Sharma, Pradeep K. [Journal of Sulfur Chemistry, 2011, vol. 32, # 4, p. 315 - 326]
[21]Location in patent: scheme or table Banerji, Jayshree; Banerji; Kotai, Laszlo; Sharma, Deepika; Sharma, Pradeep K. [Journal of the Indian Chemical Society, 2011, vol. 88, # 12, p. 1879 - 1886]
[22]Mathur, Lokesh; Choudhary; Prakash, Om; Sharma, Pradeep K. [Asian Journal of Chemistry, 2014, vol. 26, # 9, p. 2597 - 2603]
[23]Gu, Yifan; Ellis-Guardiola, Ken; Srivastava, Poonam; Lewis, Jared C. [ChemBioChem, 2015, vol. 16, # 13, p. 1880 - 1883]
  • 7
  • [ 3704-28-7 ]
  • 2-((S)-Methanesulfinyl)-benzoic acid methyl ester [ No CAS ]
  • [ 4850-73-1 ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -17℃; for 7h; Yield given. Yields of byproduct given;
With sodium phosphate buffer; H64L myoglobin mutant; dihydrogen peroxide at 25℃;
With dihydrogen peroxide In methanol; water at 25℃; for 4.5h;
Stage #1: methyl 2-(methylthio)benzoate With manganese(II) triflate; N1,N2-bis(2-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)phenyl)benzene-1,2-diamine In acetonitrile at 20℃; for 6h; Inert atmosphere; Green chemistry; Stage #2: With 1-Adamantanecarboxylic acid; dihydrogen peroxide In isopropyl alcohol; acetonitrile at -20℃; for 2h; Inert atmosphere; Green chemistry; Overall yield = 95 %; Overall yield = 79.1 mg; Optical yield = 80 %ee; enantioselective reaction;
With manganese(II) triflate; 1-Adamantanecarboxylic acid; C30H34N4O2; dihydrogen peroxide In isopropyl alcohol; acetonitrile at -20℃; for 2h; Overall yield = 95 %; Optical yield = 80 %ee; 2.10 example 2 chiral ;igand L2-Mn(OTf)2 catalytic asymmetric oxidation reaction In reaction flask by adding Mn(OTf)2 , ligand L2 and acetonitrile, the reaction mixture stirring at room temperature 6h. then adding isopropanol, sulfide substrate and adamantane formic acid and reduce the reaction temperature to -20 degrees and quickly adding hydrogen peroxide, maintain the reaction temperature 2 h, the end of the reaction add saturated NaHCO3 solution, ethyl acetate extraction, reduce under pressure , column chromatography separation product.

  • 8
  • [ 3704-28-7 ]
  • [ 118-92-3 ]
  • [ 492-22-8 ]
  • [ 67373-13-1 ]
YieldReaction ConditionsOperation in experiment
1: 4% 2: 42% With isopentyl nitrite In 1,4-dioxane; 1,2-dichloro-ethane Heating;
  • 9
  • [ 865-33-8 ]
  • [ 147-93-3 ]
  • [ 107-31-3 ]
  • [ 3704-28-7 ]
  • [ 3724-10-5 ]
YieldReaction ConditionsOperation in experiment
1: 30% 2: 65% With carbon monoxide In methanol at 150℃; for 15h;
  • 10
  • [ 3704-28-7 ]
  • [ 74-88-4 ]
  • [ 6518-72-5 ]
YieldReaction ConditionsOperation in experiment
71% With magnesium In diethyl ether for 1h; Heating;
  • 11
  • methyl 2-methylsulfinylbenzoate [ No CAS ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
94% With bis(N,N-dimethylformamide)dichloridodioxidomolybdenum(VI); glycerol In toluene at 230℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;
87% With MoO<SUB>2</SUB>Cl<SUB>2</SUB>(dmf)<SUB>2</SUB> In toluene at 140℃; for 0.166667h; Microwave irradiation;
In benzene Irradiation;
  • 12
  • [ 3704-28-7 ]
  • [ 33384-77-9 ]
YieldReaction ConditionsOperation in experiment
97% With lithium aluminium tetrahydride In tetrahydrofuran at 75℃;
96% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h;
89% With lithium aluminium tetrahydride
87% Stage #1: methyl 2-(methylthio)benzoate With diisobutylaluminium hydride In toluene at -78℃; for 3.5h; Stage #2: With isopropyl alcohol at -78 - 0℃; 146.1 Step 1 Step 1 To a solution of 2-methylsulfanylbenzoic acid methyl ester (0.30 g, 1.7 mmol) in toluene (3.0 mL), diisobutylaluminum hydride (0.94 mol/L toluene solution, 3.9 mL, 3.7 mmol) was added dropwise at -78 °C and the solution was stirred for 3.5 hours. The reaction mixture was added with 2-propanol (0.20 mL), warmed to 0 °C, and added with saturated aqueous potassium sodium tartrate solution to separate the mixture into organic layer and aqueous layer. The obtained organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=90/10 to 70/30) to obtain (2-methylsulfanylphenyl)methanol (0.22 g, 87%). 1H-NMR (270 MHz, DMSO-d6) δ 3.32 (s, 3H), 4.49 (d, J = 5.4 Hz, 2H), 5.22 (t, J = 5.4 Hz, 1H), 7.12-7.30 (m, 3H), 7.43 (d, J = 6.8 Hz, 1H).
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #1: methyl 2-(methylthio)benzoate With lithium aluminium tetrahydride In tetrahydrofuran Stage #2: With sulfuric acid

  • 13
  • [ 67-56-1 ]
  • [ 1442-03-1 ]
  • [ 3704-28-7 ]
  • 14
  • [ 74-88-4 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
With methanol at 100℃; im Rohr;
at 150 - 160℃; im Rohr;
  • 15
  • [ 186581-53-3 ]
  • [ 66304-01-6 ]
  • [ 60-24-2 ]
  • [ 1892-29-1 ]
  • [ 3704-28-7 ]
  • [ 5459-63-2 ]
  • 2-(2'-hydroxyethyldithio)carboxymethylbenzene [ No CAS ]
  • 16
  • [ 147-93-3 ]
  • [ 165190-62-5 ]
  • [ 74-88-4 ]
  • [ 3704-28-7 ]
  • [ 329217-03-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Thiosalicylic acid With sodium hydride In N,N-dimethyl acetamide Stage #2: 4-(benzyloxy)-2-bromo-1-nitrobenzene In N,N-dimethyl acetamide at 80℃; for 1h; Stage #3: methyl iodide In N,N-dimethyl acetamide at 20℃; for 45h; Further stages.;
  • 17
  • [ 98-01-1 ]
  • [ 3704-28-7 ]
  • 2-[1-Furan-2-yl-meth-(Z)-ylidene]-benzo[b]thiophen-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 18
  • [ 98-03-3 ]
  • [ 3704-28-7 ]
  • (Z)-2-(thiophen-2-ylmethylene)benzo[b]thiophen-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 19
  • [ 455-19-6 ]
  • [ 3704-28-7 ]
  • (Z)-2-(4-(trifluoromethyl)benzylidene)benzo[b]thiophen-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 20
  • [ 3704-28-7 ]
  • [ 130-03-0 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 21
  • [ 3704-28-7 ]
  • [ 104-87-0 ]
  • [ 97871-93-7 ]
YieldReaction ConditionsOperation in experiment
78% With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 22
  • [ 3704-28-7 ]
  • [ 459-57-4 ]
  • [ 242489-46-9 ]
YieldReaction ConditionsOperation in experiment
69% With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 23
  • [ 3704-28-7 ]
  • [ 100-52-7 ]
  • [ 63329-72-6 ]
YieldReaction ConditionsOperation in experiment
80% With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 24
  • [ 3704-28-7 ]
  • [ 123-11-5 ]
  • [ 101000-95-7 ]
YieldReaction ConditionsOperation in experiment
77% With lithium diisopropyl amide In tetrahydrofuran at 0 - 20℃; for 2h;
  • 25
  • [ 3704-28-7 ]
  • methyl 2-methylsulfinylbenzoate [ No CAS ]
  • [ 199657-02-8 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide at 20℃; for 3h;
  • 26
  • [ 147-93-3 ]
  • [ 616-38-6 ]
  • [ 3704-28-7 ]
  • [ 3724-10-5 ]
YieldReaction ConditionsOperation in experiment
87% With NaY faujasite at 150℃; for 15h;
  • 27
  • [ 67-56-1 ]
  • [ 3724-10-5 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
94% With thionyl chloride; for 16h;Reflux; Compound 1b (51.00 g, 303.19 mmol) was dissolved in methanol (1 L),Thionyl chloride (108.21 g, 909.57 mmol) was added,The reaction was heated to reflux and stirred for 16 hours.The reaction solution was concentrated to dryness and dissolved in ethyl acetate (500 mL).It was washed with saturated aqueous sodium hydrogen carbonate and the pH was adjusted to 7.The organic phase is dried over anhydrous sodium sulfate, filtered, and concentrated to dryness under reduced pressure.Compound 1c (55.00 g, pale yellow solid, 94%) was obtained.
94% With thionyl chloride; for 16h;Reflux; Compound 1b (51.00 g, 303.19 mmol) was dissolved in methanol (1 L), and sulfoxide chloride (108.21 g, 909.57 mmol) was added. The reaction mixture was heated to reflux, and stirred for 16 hr. The reaction mixture was concentrated to dryness, and dissolved in ethyl acetate (500 mL). The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate, and adjusted to pH 7. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to dryness, to give Compound 1c (55.00 g, yellowish solid, 94%). 1H NMR (400 MHz, DMSO-d6) delta 7.90 (d, J=7.6 Hz, 1H), 7.62-7.54 (m, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.23 (t, J=7.6 Hz, 1H), 3.82 (s, 3H), 2.42 (s, 3H).
  • 28
  • [ 658702-70-6 ]
  • [ 75-16-1 ]
  • [ 51-17-2 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
74% In tetrahydrofuran at 20℃; for 0.5h;
  • 29
  • [ 658702-70-6 ]
  • [ 917-64-6 ]
  • [ 51-17-2 ]
  • [ 3704-28-7 ]
  • [ 5459-63-2 ]
YieldReaction ConditionsOperation in experiment
1: 71% 2: 8% In tetrahydrofuran at 20℃; for 0.5h;
  • 30
  • [ 3704-28-7 ]
  • [ 914402-05-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: LiAlH4 / tetrahydrofuran 1.2: H2SO4 2.1: PBr3 / diethyl ether 3.1: toluene
  • 31
  • [ 3704-28-7 ]
  • [ 89981-01-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: LiAlH4 / tetrahydrofuran 1.2: H2SO4 2.1: PBr3 / diethyl ether
Multi-step reaction with 2 steps 1: LAH / tetrahydrofuran / 0.5 h / 0 °C 2: 0.69 g / PBr3 / diethyl ether / 20 °C
Multi-step reaction with 2 steps 1: LiAlH4 2: HBr / benzene
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 2: phosphorus tribromide / diethyl ether / 1 h / 0 - 20 °C

  • 32
  • [ 147-93-3 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaOH / methanol 1.2: HCl / methanol 2.1: H2SO4
Multi-step reaction with 3 steps 1: 92 percent 2: 89 percent / SOCl2 3: 95 percent
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 0.33 h / 20 °C 2: sulfuric acid / water / 5 h / 20 °C / Reflux
Multi-step reaction with 2 steps 1.1: sodium hydroxide / methanol; water / 0.25 h / 5 - 10 °C 1.2: 16 h / Reflux 2.1: thionyl chloride / 16 h / Reflux
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water; methanol / 0.25 h / 5 - 10 °C 1.2: 16 h / Reflux 2.1: thionyl chloride / 16 h / Reflux

  • 33
  • [ 3704-28-7 ]
  • 2-propylidene-benzo[<i>b</i>]thiophen-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran / 2 h / 0 - 20 °C 2: tetrahydrofuran / 13 h / -80 - 20 °C
  • 34
  • [ 3704-28-7 ]
  • 2-[2-Methyl-prop-(Z)-ylidene]-benzo[b]thiophen-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran / 2 h / 0 - 20 °C 2: tetrahydrofuran / 13 h / -80 - 20 °C
  • 35
  • [ 3704-28-7 ]
  • 2-(2,2-dimethyl-propylidene)-benzo[<i>b</i>]thiophen-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran / 2 h / 0 - 20 °C 2: tetrahydrofuran / 13 h / -80 - 20 °C
  • 36
  • [ 3704-28-7 ]
  • Ph3PCH(2-MeSC6H4) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 89 percent / LiAlH4 2: 75 percent / SOCl2 3: 62 percent / toluene / 18 h / Heating 4: butyllithium / tetrahydrofuran; hexane / 0.5 h
  • 37
  • [ 3704-28-7 ]
  • [ 134749-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 89 percent / LiAlH4 2: 75 percent / SOCl2 3: 62 percent / toluene / 18 h / Heating 4: 1.) n-BuLi / 1.) THF, hexane, room temp., 30 min., 2.) THF, hexane, 3 h
  • 38
  • [ 3704-28-7 ]
  • (2-Methylsulfanyl-benzyl)-triphenyl-phosphonium; chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 89 percent / LiAlH4 2: 75 percent / SOCl2 3: 62 percent / toluene / 18 h / Heating
  • 39
  • [ 3704-28-7 ]
  • [ 2976-66-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71 percent / Mg / diethyl ether / 1 h / Heating 2: 22 percent / 1.) Me2SBH3; 2.) propionic acid / hexane / 1.) 0 deg C, 30 min; 2.) reflux, 2 h
  • 40
  • [ 3704-28-7 ]
  • [ 6518-73-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 71 percent / Mg / diethyl ether / 1 h / Heating 2: 81 percent / acetyl bromide / 2 h / Heating
  • 41
  • [ 3704-28-7 ]
  • [ 75434-53-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) MeI, Mg / 1.) THF, reflux, 2 h, 2.) r.t., 1.5 h 2: m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature
  • 42
  • [ 65935-80-0 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: O2 / benzene / Irradiation 2: Irradiation
  • 43
  • [ 1442-03-1 ]
  • [ 3704-28-7 ]
  • 44
  • [ 7283-41-2 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
With dimethyl sulfate 66 EXAMPLE 66 The starting material was prepared as follows: By reacting thiosalicylic acid with dimethyl sulfate in the presence of tetrabutylammonium bromide, there was obtained methyl 2-(methylthio)benzoate, melting point 64° C.
  • 45
  • [ 17999-25-6 ]
  • [ 74-88-4 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol; ethyl acetate 150.A Methyl-2-(methylthio)benzoate Step A Methyl-2-(methylthio)benzoate To a solution of 160 mg (2.97 mmol) of sodium methoxide in 10 mL of methanol was added at 0°, 0.4 mL (2.97 mmol) of methyl thiosalicylate, 0.37 mL (5.97 mmol) of iodomethane and stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo, taken up in ethyl acetate, washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to give 2.10 g of the title compound. NMR (CDCl3): δ 2.44 (s, 3H), 3.90 (s, 3H), 7.14 (t, 1H), 7.27 (s, 1H), 7.45(m, 1H), 7.97 (d, 1H).
  • 46
  • [ 3704-28-7 ]
  • 3-Carbomethoxy-4-methylthioacetophenone [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% In isopropyl alcohol 3.a a. a. 3-Carbomethoxy-4-methylthioacetophenone The product is obtained by Friedal-Crafts reaction from 1-carbomethoxy-2-methylthiobenzene (CH3 COCl, CS2, AlCl3; reflux for 4 hours in water-bath). Yield: 43% (°C): 99°-102° isopropanol
  • 47
  • [ 3704-28-7 ]
  • [ 199657-02-8 ]
YieldReaction ConditionsOperation in experiment
97% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 15℃; for 5h; 1.3 Step 3 Compound 1c (55.00 g, 301.80 mmol) was dissolved in dichloromethane (1 L),Add m-chloroperbenzoic acid (153.18 g, 754.50 mmol, 80%) at 0°C,The reaction was stirred at 5-15°C for 5 hours and quenched by the addition of saturated sodium thiosulfate solution (150 mL).Adjust the pH to 8-9 with sodium carbonate solution.The organic phase was washed again with saturated aqueous sodium bicarbonate solution (500 mL).Dry over anhydrous sodium sulfate, filter, and concentrate to dryness under reduced pressure to give the crude product.The crude product was slurried with a mixed solvent of petroleum ether/ethyl acetate (200 mL, v/v=10/1) and filtered to give Compound 1d (62.90 g, white solid, 97%).
97% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 15℃; for 5h; 1.III Step III Compound 1c (55.00 g, 301.80 mmol) was dissolved in dichloromethane (1 L), and m-chloroperoxybenzoic acid (153.18 g, 754.50 mmol, 80%) was added at 0 °C. The reaction mixture was stirred for 5 hr at 5-15 °C, and then a saturated solution of sodium thiosulfate (150 mL) was added to quench the reaction. The resulting mixture was adjusted with a sodium carbonate solution to pH 8-9. The organic phase was further washed with a saturated aqueous solution of sodium bicarbonate (500 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to dryness, to give a crude product. The crude product was slurried in a mixed solvent of petroleum ether/ethyl acetate (200 mL, v/v=10/1), and filtered to give Compound 1d (62.90 g, white solid, 97%). 1H NMR (400 MHz, CDCl3) δ 8.15-8.10 (m, 1H), 7.72-7.64 (m, 3H), 3.97 (s, 3H), 3.34 (s, 3H).
59% With 7H-benz<c>thioxanthen-7-one; oxygen In acetonitrile at 20℃; Sealed tube; Irradiation; General procedure E to the synthesis of sulfones General procedure: A solution of sulfides 1 (0.2 mmol, 1.0 equiv) or sulfoxides 2 (0.2 mmol, 1.0 equiv), photocatalyst (c, 5 mol%), and ACN (1 mL, 0.2 M) was sealed in an oven-dried reaction tube equipped with an oxygen balloon (gas-switch three times with oxygen balloon). The reaction was agitated under 18 W 405 nm LEDs at room temperature for 12 to 24 h. The progress of the reaction was monitored by GC-MS or/and TLC. After completion of the reaction, the solvent was removed under reduced pressure, and the crude product 3 was purified by flash silica chromatography using n-hexane and ethyl acetate as eluent (v/v, 80:20).
With 3-chloro-benzenecarboperoxoic acid In 1,4-dioxane; water at 20℃; for 4h; 13.B To a solution of 2-methylsulfanylbenzoic acid methyl ester (546 mg, 3 mmol) in dioxane (15 mL) is added MCPBA (25 % in water, 4.12 g, 6 mmol) and the mixture is stirred at ambient temperature for 4 h. NaHCθ3 solution (15 mmol in 50 mL water) is added and the suspension is extracted with EtOAc (2x). The organic layer is washed with brine, dried with MgSO4 and concentrated. The residue is purified by column chromatography to give the title compound.

  • 48
  • [ 917-64-6 ]
  • [ 3704-28-7 ]
  • [ 6518-72-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl magnesium iodide; methyl 2-(methylthio)benzoate In diethyl ether at 25℃; for 3h; Reflux; Stage #2: With sulfuric acid; water In diethyl ether Cooling with ice;
  • 49
  • [ 101-81-5 ]
  • [ 3704-28-7 ]
  • [ 1169764-38-8 ]
YieldReaction ConditionsOperation in experiment
86% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; iron(II) chloride In 1,2-dichloro-ethane at 100℃; for 36h; Inert atmosphere; regioselective reaction;
  • 50
  • [ 610-97-9 ]
  • [ 67-68-5 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
71% With zinc(II) fluoride; copper(I) bromide at 150℃; for 36h; Sealed tube; Under air;
  • 51
  • [ 3704-28-7 ]
  • [ 520-72-9 ]
YieldReaction ConditionsOperation in experiment
53% With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; 61.1' Step 1': Benzo[/>]thiophen-3-olA solution of methyl 2-(methylthio)benzoate (4.0 g, 22.00 mmol) in THF (60 mL) was added to a solution of freshly prepared LDA (2M in THF, 17.5 mL, 35 mmol) placed at -78°C. The reaction mixture was stirred for 1 hour at -78°C, then overnight at room temperature. The reaction mixture was diluted by addition of a saturated solution of ammonium chloride (50 mL). The aqueous phase was separated and extracted with ethyl acetate (3 x 70 mL). The combined organic phases were washed with a saturated solution of sodium chloride (40 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (95 : 5 to 9 : 1) as eluent. The title product was obtained as a pink solid (1.74 g, 53%).*H NMR (CDCI3, 400 MHz) : δ (ppm) : 7.71 (d, J = 8 Hz, 1H), 7.49 (t, J = 8 Hz, 1H), 7.38 (d, J = 8 Hz, 1H), 7.17 (t, J = 8 Hz, 1H), 3.73 (s, 2H).
Multi-step reaction with 2 steps 1: durch Verseifung 2: >200
  • 52
  • [ 3704-28-7 ]
  • [ 1309209-07-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium diisopropyl amide / tetrahydrofuran / -78 - 20 °C 2: potassium carbonate / 1,2-dimethoxyethane; water / 20 - 95 °C
  • 53
  • [ 4298-52-6 ]
  • [ 3704-28-7 ]
  • [ 1359978-85-0 ]
YieldReaction ConditionsOperation in experiment
55% With [Rh(κ2P,P-DPEphos)(ν6-o-xylene)][BArF4] In o-xylene at 60℃; for 24h; Inert atmosphere; stereoselective reaction;
  • 54
  • [ 624-92-0 ]
  • [ 134-20-3 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 2-carbomethoxyaniline With tetrafluoroboric acid; acetic acid; isopentyl nitrite In water at 18℃; for 0.0833333h; Stage #2: Dimethyldisulphide With eosin Y disodium salt In dimethyl sulfoxide at 18℃; for 12h; Inert atmosphere; UV-irradiation; Schlenk technique;
71% Stage #1: 2-carbomethoxyaniline With tetrafluoroboric acid; tert.-butylnitrite In water; acetic acid at 20℃; for 0.0833333h; Green chemistry; Stage #2: Dimethyldisulphide With sodium acetate In dimethyl sulfoxide at 20℃; for 8h; Inert atmosphere; Green chemistry;
  • 55
  • [ 3704-28-7 ]
  • C22H21ClO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: magnesium; ethylene dibromide / tetrahydrofuran / Reflux 2: thionyl chloride / chloroform / 50 °C / Inert atmosphere
  • 56
  • [ 3704-28-7 ]
  • C40H34Cl2Pd2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: magnesium; ethylene dibromide / tetrahydrofuran; ethylene dibromide / Reflux 2: thionyl chloride / chloroform / 50 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0) / chloroform / 1 h
  • 57
  • [ 3704-28-7 ]
  • C22H21ClO2PdS*CH2Cl2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: magnesium; ethylene dibromide / tetrahydrofuran / Reflux 2: thionyl chloride / chloroform / 50 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0) / chloroform / 1 h
  • 58
  • [ 3704-28-7 ]
  • C21H17ClPdS3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: magnesium; lithium chloride / tetrahydrofuran / Reflux 2: thionyl chloride / chloroform / 50 °C / Inert atmosphere 3: tris-(dibenzylideneacetone)dipalladium(0) / chloroform / 1 h
  • 59
  • [ 3704-28-7 ]
  • [2-(α-chloro-benzhydryl)-phenyl]-methyl sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: magnesium; ethylene dibromide / tetrahydrofuran; ethylene dibromide / Reflux 2: thionyl chloride / chloroform / 50 °C / Inert atmosphere
  • 60
  • [ 108-86-1 ]
  • [ 3704-28-7 ]
  • [ 19620-59-8 ]
YieldReaction ConditionsOperation in experiment
89% With magnesium; ethylene dibromide In tetrahydrofuran; ethylene dibromide Reflux;
  • 61
  • [ 578-57-4 ]
  • [ 3704-28-7 ]
  • C22H22O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With magnesium; ethylene dibromide In tetrahydrofuran Reflux;
  • 62
  • [ 578-57-4 ]
  • [ 3704-28-7 ]
  • tris-(2-methylsulfanyl-phenyl)-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With magnesium; lithium chloride In tetrahydrofuran Reflux;
  • 63
  • [ 3704-28-7 ]
  • (3,5-bis(trifluoromethyl)phenyl)(cyano)-l3-iodanyl trifluoromethanesulfonate [ No CAS ]
  • [ 1879-21-6 ]
YieldReaction ConditionsOperation in experiment
57% In acetonitrile at 60℃; for 12h; Inert atmosphere;
  • 64
  • [ 10218-87-8 ]
  • [ 3704-28-7 ]
  • C10H14NO2S(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; ethanol at 20℃; for 0.166667h; N-Alkylsulfoximines 6 and N-Methylsulfoximines 7 from Sulfides8; General Procedure General procedure: A 50 mL round-bottomed flask, equipped with a magnetic stir barwas charged with MeOH (6 mL) and an alkylamine 11 (2.8 mmol, 2.8 equiv) for the synthesis of 6 and methylamine (11a; 33% in EtOH,360 μL, 2.8 mmol, 2.8 equiv) for the synthesis of 7. Subsequently, bromine (80 μL, 1.4 mmol, 1.4 equiv) was added dropwise. The reactionmixture was stirred vigorously for 5 min. Afterwards, sulfide 8 (1.0mmol, 1.0 equiv) was added and the mixture was stirred for another 10 min. The reaction progress was monitored by TLC. After full consumptionof 8, the solvent was removed under reduced pressure. Theresidue was taken up in acetone (25 mL) and filtered over filter paper.The filtrate was concentrated under reduced pressure to ca. 10 mL. After the addition of K2CO3 (276.4 mg, 2.0 mmol, 2.0 equiv) and KMnO4 (474.1 mg, 3.0 mmol, 3.0 equiv), the mixture was stirred for 16 h at r.t. Then, the solvent was removed under reduced pressure,the mixture was diluted with CH2Cl2 (20 mL), and the CH2Cl2 layerwas washed with distilled H2O (30 mL). The aqueous phase was extracted with CH2Cl2 (3 × 10 mL) and the combined organic phaseswere dried (MgSO4), filtered, and concentrated under reduced pressure.The product was purified by column chromatography (silica gel,eluent: n-pentane-EtOAc) to yield N-alkylsulfoximine 6 or N-methylsulfoximine 7.
  • 65
  • [ 3704-28-7 ]
  • mer-[Rh(κ3-P,O,P-(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene))(η2-PhCCPh)][BArF4] [ No CAS ]
  • mer-[Rh(κ3-P,O,P-(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene))(σ,κ1-C6H4COOMe)(SMe)][BArF4] [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% In chlorobenzene at 80℃; for 0.5h; Sealed tube; Inert atmosphere;
  • 66
  • [ 591-50-4 ]
  • [ 4892-02-8 ]
  • [ 3704-28-7 ]
  • [ 35190-68-2 ]
  • [ 67373-13-1 ]
YieldReaction ConditionsOperation in experiment
1: 77% 2: 3% 3: 3% With bis(1,5-cyclooctadiene)nickel (0); C24H20O3P2; potassium hydroxide In dimethylsulfoxide-d6 at 80℃; for 1h; Inert atmosphere;
1: 22% 2: 9% 3: 3% With bis(1,5-cyclooctadiene)nickel (0); C24H20O3P2; potassium hydroxide In dimethylsulfoxide-d6 at 80℃; for 1h; Inert atmosphere;
  • 67
  • [ 591-50-4 ]
  • [ 4892-02-8 ]
  • [ 3704-28-7 ]
  • [ 67373-13-1 ]
YieldReaction ConditionsOperation in experiment
1: 25% 2: 1% With bis(1,5-cyclooctadiene)nickel (0); C24H20O3P2; potassium hydroxide In dimethylsulfoxide-d6 at 120℃; Inert atmosphere;
  • 68
  • [ 4892-02-8 ]
  • [ 844443-04-5 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
With C24H20O3P2; potassium hydroxide In dimethylsulfoxide-d6 at 120℃; for 1h; Inert atmosphere;
  • 69
  • [ 3704-28-7 ]
  • [ 133745-75-2 ]
  • methyl 2-(((N-(phenylsulfonyl)phenylsulfonamido)methyl)thio)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% In acetonitrile at 80℃; for 1h; Sealed tube; regiospecific reaction; 25 4.4. Procedure for the sulfur-directed C(sp3)-H imidation General procedure: Procedure A: To a 10-mL reaction tube was sequentially added sulfide 1 (0.5 mmol), dry acetonitrile (1 mL), and N-fluorobis(benzenesulfonyl)imide (189 mg, 0.6 mmol). The system was quickly sealed with a Teflon cap and immersed into an 80°C oil-bath. After stirring for 1 h, dichloromethane (5 mL) was added, and the solution was transferred to a 25-mL flask. The solvent was removed under reduced pressure. The residue was purified by column chromatography with a mixture of PE and EA as eluent to afford the desired imidation product 2, of which the yield was calculated based on the sulfide. Procedure B: To a 10-mL reaction tube was sequentially added sulfide 1 (0.5mmol), dry acetonitrile (1mL), and N-fluorobis(benzenesulfonyl)imide (79 mg, 0.25 mmol). The same procedure as described above afforded the desired product 2, of which the yield was calculated based on NFSI. Caution: The reaction scale and amount of sulfides, NFSI, or acetonitrile in Procedure A and Procedure B should be adjusted according to the footnotes in Table 2.
  • 70
  • [ 67-68-5 ]
  • Potassium; 2-methoxycarbonyl-benzoate [ No CAS ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
67% With 1,10-Phenanthroline; zinc trifluoromethanesulfonate; copper(I) bromide at 170℃; for 36h; Molecular sieve;
  • 71
  • [ 3704-28-7 ]
  • [ 1127-35-1 ]
  • 72
  • [ 3704-28-7 ]
  • C17H12FNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C
  • 73
  • [ 3704-28-7 ]
  • C21H18FNO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C
Multi-step reaction with 4 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C
  • 74
  • [ 3704-28-7 ]
  • C19H14FNO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C 5: lithium hydroxide; water / tetrahydrofuran / 2 h / 25 °C
Multi-step reaction with 5 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C 5: lithium hydroxide; water / tetrahydrofuran / 2 h / 25 °C
  • 75
  • [ 3704-28-7 ]
  • C21H20FNO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C 5: palladium 10% on activated carbon; hydrogen / water; ethanol; ethyl acetate / 16 h / 25 °C / 775.74 Torr
Multi-step reaction with 5 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C 5: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 16 h / 25 °C / 775.74 Torr
  • 76
  • [ 3704-28-7 ]
  • C19H16FNO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C 5: palladium 10% on activated carbon; hydrogen / water; ethanol; ethyl acetate / 16 h / 25 °C / 775.74 Torr 6: lithium hydroxide; water / tetrahydrofuran / 2 h / 25 °C
Multi-step reaction with 6 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 0 - 15 °C 2: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 15 °C 3: trifluoroacetic acid / 1,2-dichloro-ethane / 16 h / 50 °C 4: caesium carbonate / N,N-dimethyl-formamide / 16 h / 15 - 20 °C 5: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 16 h / 25 °C / 775.74 Torr 6: lithium hydroxide; water / tetrahydrofuran / 2 h / 25 °C
  • 77
  • [ 3704-28-7 ]
  • [ 864265-08-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / 1,4-dioxane; water / 4 h / 20 °C 2: lithium borohydride / tetrahydrofuran / 14.75 h / 20 - 65 °C
  • 78
  • [ 624-92-0 ]
  • methyl 2-[(methylsulfonyl)diazenyl]benzoate [ No CAS ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
50% In acetonitrile at 20℃; for 12h; UV-irradiation; Photoinduced Synthesis of Aryl Thioethers 5; General Procedure General procedure: A solution of arylazo sulfone 1 (0.20 mmol) and the respective disulfide 4 (0.40 mmol, 2.00 equiv) in degassed MeCN (2.00 mL, 0.1 M) was poured into a glass vessel, capped, and exposed to blue light (H150 Kessil lamp, 34 W, 420 nm) at r.t. for 12 h. After the completion of the reaction (detected by TLC), the solvent was removed in vacuo, and the crude product was purified by column chromatography on silica gel.
  • 79
  • [ 3704-28-7 ]
  • [ 145490-75-1 ]
  • methyl 2-(S-methyl-N-(phenylsulfonyl)sulfinimidoyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With copper dichloride In acetone at 60℃; for 6h; 4.3. General procedure for the imination of sulfides (given in Table 3) General procedure: To a suspension of the sulfide (1.0 mmol), N-fluoro benzenesulfonamide (1.2 mmol) in t-BuOH (5 mL) was added CuCl2 (13 mg, 10 mol%) at room temperature, and the mixture was stirred for 6 h at 110 °C. The resulting suspension was purified by column chromatography (eluent: petroleum ether/ethyl acetate, 4:1) to give the corresponding sulfilimines 4a-4m.
  • 80
  • [ 3704-28-7 ]
  • [ 54705-16-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / 1,4-dioxane; water / Reflux 2: triethylamine / tetrahydrofuran / Inert atmosphere 3: triethylamine; ammonium chloride
  • 81
  • [ 3704-28-7 ]
  • C11H12O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / 1,4-dioxane; water / Reflux 2: triethylamine / tetrahydrofuran / Inert atmosphere
  • 82
  • [ 3704-28-7 ]
  • [ 2054-35-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 2.1: pyridinium chlorochromate / dichloromethane / 12 h / 0 - 20 °C 3.1: dichloromethane / 12 h / 0 - 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / 0 - 20 °C 5.1: triethylamine; methanesulfonyl chloride / dichloromethane / 12 h / 0 - 20 °C 5.2: 2 h / 90 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 7.1: bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane; lithium hexamethyldisilazane / toluene / 12 h / 100 °C / Glovebox; Inert atmosphere
  • 83
  • [ 3704-28-7 ]
  • [ 51384-29-3 ]
  • methyl 2-(((4-methylpyridin-2-yl)methyl)thio)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In dichloromethane at 0 - 30℃; Sealed tube; Irradiation;
  • 84
  • [ 420-04-2 ]
  • [ 3704-28-7 ]
  • methyl 2-(N-cyano-S-methylsulfinimidoyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tetramethyl ammonium acetate In methanol; acetonitrile at 20℃; Electrochemical reaction;
  • 85
  • [ 512-56-1 ]
  • [ 4892-02-8 ]
  • [ 3704-28-7 ]
YieldReaction ConditionsOperation in experiment
88% With calcium hydroxide In N,N-dimethyl-formamide at 80℃; for 1h; Sealed tube; General Methylation Procedure A (DMF Conditions) General procedure: A 10-mL glass reaction tube fitted with a resealable Teflon valve wasequipped with a magnetic stir bar and charged with the heteroatomnucleophile substrate (1.0 mmol, 1.0 equiv), Ca(OH)2 (100 mg, 1.35mmol, 1.35 equiv), TMP (0.20 mL, 1.7 mmol, 1.7 equiv), and DMF (1.0mL). The flask was sealed and stirred at 80 °C (or at RT for some thiolsubstrates) until TLC indicated complete conversion. The reaction wasthen worked up as described below. Workup Procedure A After complete conversion, 1 N HCl (5 mL) was added and the mixturewas extracted with CH2Cl2 (10 mL). The organic phase was separated,washed with H2O (20 mL), dried over Na2SO4, filtered, and then concentratedin vacuo. The resulting residue was purified by silica gelcolumn chromatography to afford the desired methylated product.Workup Procedure B After complete conversion, petroleum ether (5 mL) was added, andthe solid was smashed into fine particles using a spatula and sonicatedfor 5 min. The resulting residue was then directly subjected to silicagel column chromatography to afford the desired methylated product.Workup Procedure C After complete conversion, CH2Cl2 (5 mL) was added, and the mixturewas filtered through a pad of Celite, washed with H2O (10 mL), andextracted with EtOAc (5 × 20 mL). The organic phase was separated,dried over Na2SO4, filtered, and concentrated in vacuo. The resultingresidue was purified by silica gel column chromatography to affordthe desired methylated product.
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