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[ CAS No. 371-42-6 ] {[proInfo.proName]}

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Chemical Structure| 371-42-6
Chemical Structure| 371-42-6
Structure of 371-42-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 371-42-6 ]

CAS No. :371-42-6 MDL No. :MFCD00004846
Formula : C6H5FS Boiling Point : -
Linear Structure Formula :- InChI Key :OKIHXNKYYGUVTE-UHFFFAOYSA-N
M.W : 128.17 Pubchem ID :67789
Synonyms :

Calculated chemistry of [ 371-42-6 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 33.65
TPSA : 38.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 2.18
Log Po/w (WLOGP) : 2.53
Log Po/w (MLOGP) : 2.97
Log Po/w (SILICOS-IT) : 2.6
Consensus Log Po/w : 2.43

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.56
Solubility : 0.351 mg/ml ; 0.00274 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.302 mg/ml ; 0.00235 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.75
Solubility : 0.229 mg/ml ; 0.00179 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.02

Safety of [ 371-42-6 ]

Signal Word:Danger Class:3
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235 UN#:3336
Hazard Statements:H225-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 371-42-6 ]

* 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 [ 371-42-6 ]

[ 371-42-6 ] Synthesis Path-Downstream   1~93

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  • [ 90357-51-0 ]
  • [ 90356-78-8 ]
YieldReaction ConditionsOperation in experiment
98% Example 1 Preparation of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide A solution of 4-fluorobenzenethiol (21g) in methanol (65 ml) was cooled to 0° C. and aqueous 50percent sodium hydroxide (14 g) was added portionwise. The mixture was stirred at 0° C. for 30 minutes, then at 25° C. for 1 hour. To the mixture, N-[4-cyano-3-trifluoromethylphenyl]-2-methyloxiranecaboxamide (40 g) was added and the resulting mixture was stirred at room temperature for 2h. The reaction was determined to complete by TLC. Water (100 ml) was added to the mixture, followed by concentrated hydrochloric acid to a pH below 7. The solution was distilled under vacuum until no methanol distilled ceased, and the resulting suspension was stirred at 5° C. for 3 hours. The solid was collected by filtration and rinsed with water (2*40 ml). The solid was dried under vacuum at 50-60° C. to give 58 g (98percent) of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide.
93.9% Example 2-1 The title compound is prepared according to the method described in J. Med. Chem., 1988, 954-959. NaH (1.86 g, 46.5 mmol) and THF (30 ml) were charged in a 200 ml four-neck flask, and the mixture was stirred under ice-cooling. 4-Fluorothiophenol (5.16 g, 40.3 mmol) was diluted with THF (30 ml) and the solution was added dropwise. After stirring for 30 min, 4-cyano-N-(2,3-epoxy-2-methylpropionyl)-3-trifluoromethylaniline (10.37 g, 38.4 mmol) was dissolved in THF (50 ml) and the solution was added dropwise. After stirring for 1 hr, the bath was removed and the mixture was stirred overnight at room temperature. Saturated brine (40 ml) and toluene (40 ml) were added and the mixture was partitioned. Saturated brine (20 ml) and ethyl acetate (80 ml) were added to the organic layer and the mixture was neutralized with 5N HCl. After partitioning, the organic layer was washed twice with saturated brine (30 ml), dried over MgSO4, decolorized with activated carbon (carborafine 0.5 g) and concentrated under reduced pressure to give a residue. Toluene (30 ml) was added to the residue, and n-heptane (22 ml) was added dropwise at a temperature of 70° C.-65° C. After the completion of dropwise addition, the mixture was cooled to room temperature and filtrated to give the objective compound (15.74 g, yield 93.9percent). Purity 98.7percent.
92.5% With potassium carbonate; In acetone; at 10 - 20℃; 250 ml of Acetone and 25 gm of N-[4-cyano-3-(trifluoromethyl)phenyl]-2-Methyloxirane-2-carboxamide (1) charged into a 500 ml flask at room temperature under stirring and stirred till to obtain the clear solution. 9.8 gm of Potassium Carbonate was added and cooled the reaction mixture to 10-15° C. under stirring. Added 15 gm 4-Fluorothiophenol slowly through addition tank in 3-4 hours at 10-15° C. under stirring. Removed the cooling and brought the reaction mixture to RT under stirring and stirred for 2-3 hours at RT while monitoring the reaction by HPLC for the presence of unreacted -N-[4-cyano-3-(trifluoro methyl)phenyl]-2-Methyloxirane-2-carboxamide (1) (unreacted compound (1) <0.50percent]. Filter the reaction mixture over Nutsche Filter and wash with 50 ml acetone. Acetone was later on recovered completely at 40-50° C. under vacuum until dryness. To this dried residue, 250 ml DM water was added and stirred the solution for 4-5 hours at RT. About 125 ml Toluene was added to this solution and stirred the reaction mixture for 10-12 hours. The reaction mixture was filtered and washed with 50 ml Toluene. The solid was dried for 6-7 hours under vacuum. 34 gm solid was obtained ; Yield -92.5percent, Water content -0.2percent w/w; Purity -99.0percent by HPLC.
91.5% 20 kg of ethyl acetate was added to a 50 L glass reactor, and the high-low temperature cooling and heating machine was turned on, and the temperature of the reaction system was cooled to 0 to 5 ° C.100 g of sodium methoxide was added to the reaction vessel, and 1.05 kg of 4-fluorothiophenol was added dropwise slowly, and the addition was completed in about 1.5-2 hours, and stirring was continued at the temperature for 0.5 h.Then, 2.0 kg of N-[4-cyano-3-(trifluoromethyl)phenyl]-1,2-epoxy-2-methylpropanamide was added in portions.After the addition, the reaction system was warmed to room temperature.TLC followed the progress of the reaction. After 0.5 h of reaction, the reaction was completed and washed 3 times with saturated brine.The ethyl acetate was distilled off under reduced pressure to evaporate, and 8 kg of ethanol was added to dissolve, and the crystal was cooled and cooled at 0 to 5 ° C, filtered, and dried at 60 ° C.2.7 kg of N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[4-fluorophenylthio]-2-hydroxy-2-methylpropanamideThe yield was 91.5percent.
90.2% With sodium hydroxide; In tetrahydrofuran; water; ethyl acetate; at 5 - 10℃; for 2h;Product distribution / selectivity; Example 2-2 [0224] 4-Fluorothiophenol (2.79 g, 21.8 mmol) and THF (30 ml) were charged in a 100 ml four-neck flask, and the mixture was stirred under ice-cooling. 20percent Aqueous NaOH solution (5.0 g, 25.0 mmol) was added dropwise thereto. 4-Cyano-N-(2,3-epoxy-2-methylpropionyl)-3-trifluoromethyl aniline (5.59 g, 20.7 mmol) was dissolved in THF (25 ml) and the solution was added dropwise at a range of 5[deg.] C.-10[deg.] C. After stirring for 2 hr, toluene (15 ml) and saturated brine (15 ml) were added and the mixture was partitioned. Saturated brine (20 ml) was added to the organic layer, and the organic layer was adjusted to pH=4 (universal test paper) with 5N HCl and washed. The mixture was dried over MgSO4, decolorized with activated carbon (carborafine 0.5 g) and concentrated under reduced pressure to give a residue. Toluene (15 ml) was added to the residue and n-heptane (10 ml) was added dropwise thereto at a temperature of 70[deg.] C.-65[deg.] C. After the completion of the dropwise addition, the mixture was allowed to cool to room temperature and filtrated to give the objective compound (7.45 g, yield 90.2percent). Purity 99.0percent.
77.4% With triethylamine; In toluene; at 20℃;Product distribution / selectivity; (3) Synthesis of 4'-cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide The reaction mixture obtained in the above-mentioned (2) was cooled to 5° C. under ice-cooling. After dropwise addition of 4-fluorothiophenol (7.60 g, 59.3 mmol) at not higher than 10° C., and Et3N (2.42 g, 23.9 mmol) was added thereto. After 1 hr, 4-fluorothiophenol (0.5 ml, 0.602 g, 4.7 mmol) was added thereto. After 1 more hour, 4-fluorothiophenol (0.5 ml, 4.7 mmol) was added and the mixture was stirred overnight at room temperature. The reaction mixture was added to saturated brine (40 ml) and partitioned. Saturated brine (40 ml) was added to the organic layer, and the mixture was adjusted to pH.approx/equal.3 (universal test paper) with 5N (mol/l) HCl and washed. After drying over MgSO4, the mixture was concentrated under reduced pressure. Toluene (50 ml) was added to the obtained residue and the mixture was heated to 70° C. Activated carbon (carborafine, 0.5 g) and gamma-alumina (1.0 g) were added, and the solution was filtrated after stirring at the above-mentioned temperature for 10 min. After allowing to cool to 20° C., the mixture was filtrated to give a sulfide form [4'-cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide] (18.19 g). Purity 98.4percent, yield 77.4percent (total yield of (1) to (3)). Example 5 [0239] Synthesis of 4'-cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide [0240] N-Methacryloyl-4-cyano-3-trifluoromethylaniline (15.0 g, 59.0 mmol) and ethyl acetate (25 ml) were charged in a 500 ml four-neck flask and the mixture was heated at 50-55[deg.] C. A solution of mono-perphthalic acid in ethyl acetate (160.14 g, net 21.49 g, 118.0 mmol) was added dropwise over 3.16 hr. After stirring at the above-mentioned temperature for 2 hr, a solution of mono-perphthalic acid in ethyl acetate (46.95 g, net 6.12 g, 33.6 mmol) was dropwise added over 1.5 hr and the mixture was stirred for 1.5 hr. The mixture was adjusted to pH=8 (universal test paper) with 20percent aqueous KOH solution (100 ml) and 10percent Na2SO3 (45.40 g) was added. The mixture was partitioned, and the organic layer was washed with a solution of Na2S2O5 (5.0 g) in deionized water (20 ml) and then dried over MgSO4. When the LC sensitivity of the epoxy form is 100percent, the diol form was 6.91percent. [0241] The obtained reaction mixture was concentrated under reduced pressure and then toluene (50 ml) was added thereto. The mixture was again concentrated under reduced pressure. Toluene (30 ml) was added thereto and the mixture was stirred under ice-cooling. MsCl (2.04 g, 17.7 mmol) and Et3N (3.58 g, 35.4 mmol) were added dropwise at not higher than 10[deg.] C. As a result of LC analysis (under the same conditions as the above-mentioned LC conditions), the diol form was 0.37percent of the epoxy form. [0242] The obtained reaction mixture was cooled to 5[deg.] C. under ice-cooling. 4-Fluorothiophenol (9.15 g, 71.4 mmol) was added dropwise thereto at not higher than 10[deg.] C. After 1 hr, 4-fluorothiophenol (0.5 ml, 0.602 g, 4.7 mmol) was further added thereto and the mixture was stirred overnight at room temperature. The reaction mixture was added to saturated brine (40 ml) and the mixture was partitioned. Saturated brine (40 ml) was added to the organic layer, and the mixture was adjusted to pH=3 (universal test paper) with 5N (mol/l) HCl and washed. After drying over MgSO4, the mixture was concentrated under reduced pressure. Toluene (50 ml) was added to the obtained residue and the mixture was heated to 70[deg.] C. Activated carbon (carborafine, 0.5 g) and [gamma]-alumina (1.0 g) were added, and the mixture was stirred at the above-mentioned temperature for 10 min, and then filtrated. After allowing to cool to 20[deg.] C., the mixture was filtrated to give a sulfide form (17.65 g). Purity 96.5percent, yield,75.1percent. Example 6 [0243] Synthesis of 4'-cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide [0244] The following reactions were carried out under a nitrogen atmosphere unless particularly specified. [0245] N-Methacryloyl-4-cyano-3-trifluoromethylaniline (15.0 g, 59.0 mmol) and ethyl acetate (40 ml) were charged in a 500 ml four-neck flask, and the mixture was heated at 50-55[deg.] C. Nitrogen was flown at a flow rate of 10 ml/min. A solution of mono-perphthalic acid in ethyl acetate (119.4 g, net 21.5 g, 118 mmol) was dropwise added and the mixture was stirred for 2 hr. Thereafter, a solution of mono-perphthalic acid in ethyl acetate (55.7 g, net 10.0 g, 55 mmol) was dropwise added and the mixture was stirred for 4 hr. After cooling to not higher than 10[deg.] C., a 15percent Na2SO3 solution (99.1 g) was added dropwise. Thereafter, a 20percent aqueous KOH solution was added dropwise and the mixture was adjusted to pH=8.3 and partitioned. The organic layer was concentrated-under reduced pressure. Toluene (50 ml) was added thereto an...
General procedure: To a mixture of NaH (60percent in mineral oil, 0.050 g, 1.23 mmol) in anhydrous THF (2 mL) at 0 °C under Ar atmosphere was added a solution of the differently substituted phenol or thiophenol (1.11 mmol) in 1 mL of anhydrous THF. This mixture was stirred at r.t. for 20 min. A solution of the different intermediate 17-21 (0.74 mmol) in anhydrous THF (3 mL) was added slowly. The reaction mixture was stirred at r.t. o.n. The mixture was then diluted with ethyl acetate (30 mL), washed with brine (15 mL) and water (30 mL), dried over Na2SO4 and concentrated under vacuum. The crude residue was purified by flash column chromatography.

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  • 3,18-didevinyl-3,18-bis[2-(pfluorothiophenyl)ethyl]bilirubin [ No CAS ]
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  • [ 98541-64-1 ]
  • 2-<i>tert</i>-butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic acid [ No CAS ]
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  • 6-formylpyridine-2-carbothionic acid-S-4-fluorophenyl ester [ No CAS ]
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  • 6-(4-fluoro-phenylsulfanyl)-9-methyl-9<i>H</i>-purine [ No CAS ]
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  • [ 13720-94-0 ]
  • ethyl 4-(4-fluorothiophenyl)quinoline-3-carboxylate [ No CAS ]
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  • [ 371-42-6 ]
  • [ 138286-76-7 ]
  • [ 212769-59-0 ]
YieldReaction ConditionsOperation in experiment
90% Example 382-(4-Fluoro-phenylsulfanyl)-octanoic acid hydroxyamide Z-(4-Fluoro-phenylsulfanyl)-octanoic acid ethyl ester was prepared according to the general method as outlined in example 9. Starting from <strong>[138286-76-7]ethyl 2-bromooctanoate</strong> (6.47 g, 24.7 mmol) and 4-fluorothiophenol (3 g, 23.4 mmol). Yield: 6.31 g (90%); clear oil; MS: 299 (M+H)+.
90% 2-(4-Fluoro-phenylsulfanyl)-octanoic acid ethyl ester was prepared according to the general method as outlined in example 9. Starting from <strong>[138286-76-7]ethyl 2-bromooctanoate</strong> (6.47 g, 24.7 mmol) and 4-fluorothiophenol (3 g, 23.4 mmol). Yield: 6.31 g (90%); clear oil; MS: 299 (M+H)+.
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YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In methanol; water; a) alpha-(p-Fluorophenylthiomethyl)acrylic acid To a solution of 3.293 kg (25.69 mol) p-fluorothiophenol in 19.3 1 methanol is added a solution of 3.32 kg (86%, 51.79 mol) potassium hydroxide in 3.32 1 water dropwise with stirring at 0 C., then a solution of 4.452 kg (26.98 mol) alpha-bromomethylacrylic acid in 4.3 1 methanol at such a rate as to maintain the reaction temperature below 15 C. The mixture is stirred for an additional 2 hours at 10 C., then poured into cold water (80 1) and acidified to pH 1 with concentrated hydrochloric acid. The product is filtered, washed with water and dried in vacuo, m.p. 110-112 C.
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  • [ 23616-57-1 ]
  • [ 633304-04-8 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; potassium carbonate; In DMF (N,N-dimethyl-formamide); at 65℃; for 4h; A solution of 3-iodo-1 H-pyrrolo [2,3-b] pyridine (4.0 g, 16.4 [MMOL)] in DMF is treated with 4-fluorobenzenethiol (2.09 mL, 19.7 mmol), potassium carbonate (3.40 g, 24.6 mmol), and copper iodide (4.21 g, 22.1 [MMOL).] The reaction mixture is heated at [65C] for 4 h, cooled, diluted with conc. aqueous NH40H and extracted with ethyl acetate. The extracts are combined, washed with brine, dried over MgS04and concentrated in vacuo. Chromatography (1: 50 methanol : [CH2CI2)] of the residue, followed by [METHANOVH20 CRYSTALLIZATION] affords the title compound as an off-white solid, 3.56 g, mp [183-184C,] characterized by mass spectral and NMR analyses.
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  • [ 85068-30-0 ]
  • [ 1055974-03-2 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 20℃; for 12h; Step A: 4-Fluorothiophenol (compound 24c; 900 muL) was dissolved in 40 mL of anhydrous THF under an atmosphere of dry nitrogen. To this solution was added 8.40 mL of potassium tert-butoxide in THF (1.0 M) followed by the addition of 10 mL of anhydrous DMF. The reaction mixture was stirred at ambient temperature for 10 minutes, after which time 1.43 g of 2,4-difluoropropiophenone was added and the mixture was allowed to react for about 12 hours at room temperature. The reaction mixture was then partitioned between Et2O and water. The Et2O layer was washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated under vacuum to provide compound 25c
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  • [ 82420-34-6 ]
  • [ 651780-34-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; for 2h; To a solution of 4-bromo-l- (bromomethyl)-2-nitrobenzene (0.60g) in tetrahydrofuran (10ml) was added 4-fluorothiophenol (1. 2ml) and diisopropylethylamine (0. 45ml). After stirring for 2h the mixture was concentrated under vacuum and purified by column chromatography on silica, eluting with petroleum ether (40- 60) : dichloromethane (9: 1 to 8: 1) to give the title compound (0.52g). LCMS: Rt 3.73 min.
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  • [ 371-42-6 ]
  • [ 870301-30-7 ]
YieldReaction ConditionsOperation in experiment
100% With potassium phosphate; copper(l) iodide; In ethylene glycol; at 20 - 80℃; for 18h; Description 11; 8-Chloro-3-[(4-fluorophenyl)thio]quinoline (D11); Successive portionwise additions of potassium phosphate (102.7g, 0.48mol), copper (I) iodide (2.3g, 12mmol) and <strong>[847727-21-3]8-chloro-3-iodoquinoline</strong> (D10) (7Og1 0.24mol) were added with stirring to ethylene glycol (1L) at ambient temperature. 4-Fluorobenzenethiol(38.6ml, 0.363mol) was added to the mixture in one portion and the whole was heated with stirring at 8O0C for 18h. The mixture was then cooled to ambient temperature and water (800ml) and dichloromethane (800ml) were added. After vigorously stirring for 20 mins, the layers were separated and the stirred organic phase was treated with charcoal (2Og). After 0.5h stirring, the mixture was filtered and the filtrate washed with water (500ml), dried and concentrated in vacuo to afford the title compound (D11 ) as a crude yellow solid (78g, 0.27mol, 100%) which was used without purification in the next stage (see D12). Mass Spectrum Ci5H9CIFNS requires 289; found 290 (MH+).
100% With potassium phosphate; copper(l) iodide; In ethylene glycol; at 20 - 80℃; for 18h; Description 4; 8-Chloro-3-[(4-fluorophenyl)thio]quinoline (D4); Successive portionwise additions of potassium phosphate (102.7 g, 0.48 mol), copper (I) iodide (2.3 g, 12 mmol) and <strong>[847727-21-3]8-chloro-3-iodoquinoline</strong> (D3) (70 g, 0.24 mol) were added with stirring to ethylene glycol (1 L) at ambient temperature. 4-Fluorobenzenethiol (38.6 ml, 0.363 mol) was added to the mixture in one portion and the whole was heated with stirring at 80C for 18h. The mixture was then cooled to ambient temperature and water (800 ml) and dichloromethane (800 ml) were added. After vigorously stirring for 20 mins, the layers were separated and the stirred organic phase was treated with charcoal (20 g). After 0.5 h stirring, the mixture was filtered and the filtrate washed with water (500 ml), dried and concentrated in vacuo to afford 8-chloro-3-[(4- fluorophenyl) thio]quinoline (D4) as a crude yellow solid (78 g, 0.27 mol, 100%) which was used without purification in the next stage (see D5). MS: m/z (M+H+) 290,292; C15H9ClFNS requires 289,291.
With potassium phosphate; copper(l) iodide; In ethylene glycol; at 20 - 80℃; for 18h; Successive portionwise additions of potassium phosphate (102.7g, 0.48mol), copper (I) iodide (2 3g, 12mmol) and <strong>[847727-21-3]8-chloro-3-iodoquinoline</strong> (7Og, 0.24mol) were added with stirring to ethylene glycol (IL) at ambient temperature. 4-Fluorobenzenethiol (38.6ml, 0 363mol) was added to the mixture in one portion and the whole was heated with stirring at 800C for 18h The mixture was then cooled to ambient temperature and water (800ml) and dichloromethane (800ml) were added. After vigorously stirring for 20 mms, the layers were separated and the stirred organic phase was treated with charcoal (2Og). After 0 5h stirring, the mixture was filtered and the filtrate washed with water (500ml), dried and concentrated in vacuo to afford the title compound as a crude yellow solid (78g, 0 27mol, 100%) which was used without purification m the next stage (see Intermediate 60). Mass Spectrum Ci5H9ClFNS requires 289; found 290 (MH+).
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YieldReaction ConditionsOperation in experiment
Example 3; N-methacryloyl-4-cyano-3-trifluoromethylaniline (57.3 g, 0.225 mol), ethyl acetate (340 ml) and phthalic anhydride (116.9g, 0.789 mol) were charged and the mixture was heated to 50 to 55°C. To the mixture was added dropwise 35percent aqueous hydrogen peroxide solution (43.8 g, 0.451 mol) over 8 hours and the mixture was matured for 20 hours. After adding ethyl acetate (114 ml), the mixture was cooled to 15°C and then aqueous solution (145 ml) of sodium sulfite (25.6 g) was added dropwise thereto. After confirming absence of the per-oxy acid, 15percent aqueous potassium hydroxide solution was added dropwise to the mixture, for adjusting pH to 7.3. Phases were separated and a layer was washed with a solution prepared from water (230 ml), sodium chloride (40.5 g) and 35percent aqueous hydrochloric acid (0.23 g). After concentrating the organic layer under reduced pressure, toluene (400 ml) was added and the layer was further concentrated. The concentrate obtained was combined with THF (344 ml) and cooled down to 5°C. Then triethylamine (11.4 g, 0.113 mol) and subsequently methanesulfonyl chloride (6.5 g, 0.056 mol) were added dropwise and the mixture was matured at the same temperature for 30 minutes. Then, a mixed solution of 4-fluorothiophenol (34.7 g, 0.27 mol) with toluene (28 ml), and subsequently triethylamine (11.4 g, 0.113 mol) were added dropwise, and the mixture was matured at the same temperature for 30 minutes. After heating to 50°C, the mixture was matured at the same temperature for 5 hours. After cooling to 15°C, the mixture was washed with 135 g of 15percent aqueous sodium chloride, then with a solution prepared from 143 ml of water, 19.5 g of sodium chloride and 7.8 g of sodium carbonate. At this point, the content of Deoxy-Sulfide Compound was 0.064percent (LC area percentage). After phase separation, the organic layer was concentrated, combined with 400 ml of toluene and concentrated further under reduced pressure. After heating to 75°C, 69 ml of toluene, 2.9 g of alumina and 3.4 g of activated carbon were added and the mixture was stirred at the same temperature for 30 minutes. After filtering while hot, the filter was washed with 57 ml of toluene and the obtained organic layer was cooled down to 55°C. After crystallization by seeding with seed crystals (0.017percent by weight), the mixture was matured at 56 to 50°C for an hour. Then, the mixture was cooled (13.3°C/hour) down to 10°C over 3 hours. After cooling, the mixture was matured at 10+/-2°C for 2 hours. Upon filtration and washing, 80.0 g of a wet cake of 4'-cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide was obtained. After drying, 76.0 g (yield: 84.6percent) of a dry cake was obtained. The content of Deoxy-Sulfide Compound in the dry cake was not detected (n.d.). To the purified and Deoxy-Sulfide Compound non-detected crystals of 4'-cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide was added Deoxy-Sulfide Compound, separately prepared, at ratios (LC area percentage (percent)) shown in Table 1. Using the obtained crystals of 4'-cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide, the experiments were conducted in the same manner as in Example 2 to give crystals of 4'-cyano-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-3'-trifluoromethylpropionanili de. The results are shown in Table 1.; Example 4; N-methacryloyl-4-cyano-3-trifluoromethylaniline (1 part by weight), ethyl acetate (5.4 parts by weight) and phthalic anhydride (2 parts by weight) were charged and the mixture was heated to 50 to 55°C. To the mixture was added dropwise 35percent aqueous hydrogen peroxide solution (0.57 part by weight) over 9.7 hours and the mixture was matured for 22.3 hours. After adding ethyl acetate (1.8 parts by weight), the mixture was cooled to 15°C and then aqueous solution (1 part by weight) of sodium sulfite (0.17 part by weight) was added dropwise thereto. After confirming absence of the per-oxy acid, 15percent aqueous potassium hydroxide solution was added dropwise to the mixture, for adjusting pH to 7.0. Phases were separated and a layer was washed with a solution prepared from water (4 parts by weight), sodium chloride (0.7 part by weight) and 35percent aqueous hydrochloric acid (0.004 part by weight). After concentrating the organic layer under reduced pressure, toluene (6 parts by weight) was added and the layer was further concentrated. The concentrate was combined with THF (5.3 parts by weight) and cooled down to 5°C. Then triethylamine (0.08 parts by weight) and subsequently methanesulfonyl chloride (0.045 parts by weight) were added dropwise and the mixture was matured at the same temperature for 30 minutes. Then, a mixed solution of 4-fluorothiophenol (0.6 part by weight) with toluene (0.43 part by weight), and subsequently triethylamine (0.2 part by weight) were added dropwise, and the mixture was matured at the same temperature fo...
  • 23
  • [ 1722-10-7 ]
  • [ 371-42-6 ]
  • [ 454181-94-3 ]
YieldReaction ConditionsOperation in experiment
85% In N,N-dimethyl-formamide; Step 1: 3-(2-Fluoro-phenylsulfanyl)-6-methoxy-pyridazine. To a clear solution of 4-fluorothiophenol (2.56 g) in DMF (10 mL) was added 3-chloro-6-methoxy-pyridazine (3.18 g) and stirred at room temperature for 1 hour. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (50 mL). The ethyl acetate layer was collected, washed with water (2*20 mL) and the organic portion was collected, dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated to obtain crude 3-(2-fluoro-phenylsulfanyl)-6-methoxy-pyridazine (85%, 4.0 g, mp, 58-62 C.; mass spectrum M+, 236).
85% In N,N-dimethyl-formamide; Step A: 3-(2-Fluoro-phenylsulfanyl)-6-methoxy-pyridazine. To a clear solution of 4-fluorothiophenol (2.56 g) in DMF (10 mL) was added 3-chloro-6-methoxy-pyridazine (3.18 g) and stirred at room temperature for 1 hour. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (50 mL). The ethyl acetate layer was collected, washed with water (2*20 mL) and the organic portion was collected, dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated to obtain crude 3-(2-fluoro-phenylsulfanyl)-6-methoxy-pyridazine (85%, 4.0g, mp, 58-62 C.; mass spectrum M+, 236).
85% In N,N-dimethyl-formamide; Step A 3-(2-Fluoro-phenylsulfanyl)-6-methoxy-pyridazine . To a clear solution of 4-fluorothiophenol (2.56 g) in DMF (10 mL) was added 3-chloro-6-methoxy-pyridazine (3.18 g) and stirred at room temperature for 1 hour. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (50 mL). The ethyl acetate layer was collected, washed with water (2X20 mL) and the organic portion was collected, dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated to obtain crude 3-(2-fluoro-phenylsulfanyl)-6-methoxy-pyridazine (85%, 4.0g, mp, 58-62C; mass spectrum M+, 236).
  • 24
  • [ 371-42-6 ]
  • [ 36314-97-3 ]
  • [ 881193-21-1 ]
YieldReaction ConditionsOperation in experiment
64% In isopropyl alcohol; at 80℃; for 6h; 4-(4-Fluoro-phenylsulfanyl)-6-phenyl-pyrimidin-2-ylamine was prepared from 4-Chloro-6-phenyl-pyrimidin-2-ylaniine (0.5 g, 2.44 mmol) using 4-fluorothiophenol (0.31 mg, 2.44 mmol) in zso-propanol (15 mL) at 800C for 6 hours. Yield: 64%. M.P.: 218-2200C.1H NMR (200 MHz, DMSO-J5): delta 7.94 (d, J= 6.2 Hz, 2H), 7.76 (d, J- 5.4 Hz, 2H), 7.74-7.34 (m5 5H), 6.50 (s, IH). LR: (KBr) 3489, 3246, 1674. MS: m/z (CI) 298 (M+, 100%).
  • 25
  • [ 371-42-6 ]
  • [ 76-04-0 ]
  • [ 911360-86-6 ]
YieldReaction ConditionsOperation in experiment
90% 4-Fluorothiophenol (1.64 ml_, 15.3 mmol) and <strong>[76-04-0]2-<strong>[76-04-0]chloro-2,2-difluoroacetic acid</strong></strong>(1.47 mL, 15.3 mmol) were dissolved in dioxane, cooled to O0C, and sodium hydride (60%,1.28g, 32.1 mmol) was added. The mixture was then raised to room temperature and, when bubbling had ceased, was heated at 100 0C for 3 hours. The mixture was then cooled to room temperature, 5 mL of ethanol was added, and the suspension poured into a mixture of ice in 1 N HCI. The mixture was then extracted with ethyl acetate and the organic layer v/ashed with water, then brine and dried (MgSO4). The residue was triturated with hexanes; the solvent was removed to afford 209 as a beige solid (3.05g, 90%). LRMS (ESI): (calc)222.0; (found) 220.9 (M)"
  • 26
  • [ 371-42-6 ]
  • [ 13421-00-6 ]
  • [ 12775-96-1 ]
  • [ 54435-13-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In water; A solution of 214 g. of potassium hydroxide and 2 l. of water is reacted with 122 g. of 4-fluoro-(thiophenol) under an atmosphere of nitrogen at 50 and stirred for 15 minutes. After the addition of 3 g. of copper powder and 2.69 g. of <strong>[13421-00-6]5-chloro-2-iodo-<strong>[13421-00-6]benzoic acid</strong></strong>, the reaction mixture is heated under reflux conditions for 7 hours. The entire mixture is filtered warm and the filtrate acidified with hydrochloric acid. The resulting precipitate is filtered, washed neutral with water and evaporated under reduced pressure, whereby there is obtained 3-chloro-6-[(4'-fluorophenyl)-thio]-<strong>[13421-00-6]benzoic acid</strong>, having a melting point of 176-177.
  • 27
  • [ 371-42-6 ]
  • [ 13421-00-6 ]
  • [ 54435-72-2 ]
YieldReaction ConditionsOperation in experiment
The starting material 2,10-dichloro-8-fluoro-10,11-dihydrodibenzo[b,f]thiepin can be prepared from <strong>[13421-00-6]5-chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong></strong> and 4-fluoro-(thiophenol) in a similar manner to that described in example 1. The following intermediates are obtained: 3-chloro-6-[(4'-fluoro-phenyl)-thio]-<strong>[13421-00-6]benzoic acid</strong>; melting point 176-177. 3-chloro-6-[(4'-fluoro-phenyl)-thio]-benzyl alcohol (brown oil). 3-chloro-6-[(4'-fluoro-phenyl)-thio]-benzyl chloride (brown oil). 3-chloro-6-[(4'-fluoro-phenyl)-thio]-phenyl acetonitrile (dark brown oil). 3-chloro-6-[(4'-fluoro-phenyl)-thio]-phenyl acetic acid; melting point after recrystallisation from benzene/hexane 93. 2-chloro-8-fluoro-dibenzo[b,f]thiepin-10(11H)-one. melting point 132. 2-chloro-8-fluoro-10,11-dihydro-dibenzo[b,f]thiepin-10-ol; melting point 90. The obtained 2,10-dichloro-8-fluoro-10,11-dihydro-dibenzo[b,f]thiepin consists of white crystals melting at 84-85.
  • 28
  • [ 590-92-1 ]
  • [ 371-42-6 ]
  • p-fluorophenylthiopropionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% In sodium hydroxide; A. p-fluorophenylthiopropionic acid To a solution of 10 g. of p-fluorothiophenol in 156 ml. of 1N aqueous sodium hydroxide is added 11.95 g. of beta-<strong>[590-92-1]bromopropionic acid</strong>, and the reaction stirred for 90 min. The reaction mixture is acidified to pH 4.0-5.0 with 6N hydrochloric acid and the reaction stored in the cold over a weekend. The resulting precipitate is filtered, washed with water and dried to give 13.8 g. (88% yield) of the intermediate, m.p. 67-69 C.
  • 29
  • [ 371-42-6 ]
  • [ 56096-89-0 ]
  • [ 60086-46-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;copper(I) chloride; In pyridine; sodium hydrogencarbonate; EXAMPLE 23 To a solution of 3.28 g. (0.0256 mol) of p-fluorothiophenol and 6.8 g. (0.0256 mol) of <strong>[56096-89-0]2-iodo-4-fluorobenzoic acid</strong> in 40 ml. of pyridine is added 3.54 g. (0.0256 mol) of potassium carbonate at room temperature with stirring. Additional pyridine is added to dissolve the precipitate and then 1.54 g. of cuprous chloride is added. The mixture is refluxed overnight, cooled, poured into ice-water, stirred and filtered. The aqueous solution is acidified, filtered and the solid dissolved in 5% sodium bicarbonate solution, then extracted with ether. The aqueous solution is acidified, extracted with ether, and the dried extract is concentrated to give 4-fluoro-2-(4-fluorophenylthio)benzoic acid, m.p. 209-218 C.
  • 30
  • [ 316373-95-2 ]
  • [ 371-42-6 ]
  • [ 7440-44-0 ]
  • [ 90356-78-8 ]
YieldReaction ConditionsOperation in experiment
In sodium hydroxide; water; ethyl acetate; isopropyl alcohol; Petroleum ether; Example 7 N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide Under nitrogen, to a solution of 25.6 g (0.20 mol) of 4-fluorthiophenol in 500 ml of isopropanol 8.4 g (0.20 mol) of sodium hydroxide in 400 ml of water was added. The mixture was stirred at 25 °C for 2 h, then 58.6 g (16 mmol) of N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-(methanesulfonyloxy)-2-methyl-propionamide in 500 ml of isopropanol was added. Then the mixture was stirred at 25°C for 5 h, then the pH was adjusted to neutral with concentrated hydrochloric acid and treated with charcoal at reflux temperature. Most of the isopropanol was evaporated in vacuum and 250 ml of 2percent aqueous sodium hydroxide solution was added to the residue under vigorous stirring, then the crystalline mixture was left for I h, then filtered and washed with water. The dried crystals were recrystallized from a 1:4 mixture of ethyl acetate / petroleum ether, which has a boiling range of 40-70°C.
  • 31
  • [ 212769-59-0 ]
  • [ 371-42-6 ]
  • [ 138286-76-7 ]
  • 2-(4-fluoro-phenylsulfanyl)-octanoic acid hydroxyamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 38 2-(4-Fluoro-phenylsulfanyl)-octanoic acid hydroxyamide 2-(4-Fluoro-phenylsulfanyl)-octanoic acid ethyl ester was prepared according to the general method as outlined in example 9. Starting from <strong>[138286-76-7]ethyl 2-bromooctanoate</strong> (6.47 g, 24.7 mmol) and 4-fluorothiophenol (3 g, 23.4 mmol). Yield: 6.31 g (90%); clear oil; MS: 299 (M+H)+. Starting from 2-(4-fluoro-benzenesulfanyl)-octanoic acid ethyl ester (3.1 gm, 10 mmol) 2.89 g (Yield: 100%) of 2-(4-fluoro-benzenesulfanyl)-octanoic acid was isolated as colorless semi-solid by following the procedure as outlined in example 9. MS: 268.9 (M+H)+. Starting from 2-(4-fluoro-benzenesulfanyl)-octanoic acid (2.49 g, 9.2 mmol) and following the procedure as outlined in example 1, 2.72 g of 2-(4-fluoro-benzenesulfanyl)-octanoic acid hydroxyamide was isolated as colorless solid. Yield: 99%, MP: 58 C; MS: 284 (M-H).
EXAMPLE 38 2-(4-Fluoro-phenylsulfanyl)-octanoic acid hydroxyamide 2-(4-Fluoro-phenylsulfanyl)-octanoic acid ethyl ester was prepared according to the general method as outlined in example 9. Starting from <strong>[138286-76-7]ethyl 2-bromooctanoate</strong> (6.47 g, 24.7 mmol) and 4-fluorothiophenol (3 g, 23.4 mmol). Yield: 6.31 g (90%); clear oil; MS: 299 (M+H)+. Starting from 2-(4-fluoro-benzenesulfanyl)-octanoic acid ethyl ester (3.1 gm, 10 mmol) 2.89g (Yield: 100%) of 2-(4-fluoro-benzenesulfanyl)-octanoic acid was isolated as colorless semi-solid by following the procedure as outlined in example 9. MS: 268.9 (M+H)+. Starting from 2-(4-fluoro-benzenesulfanyl)-octanoic acid (2.49 g, 9.2 mmol) and following the procedure as outlined in example 1, 2.72 g of 2-(4-fluoro-benzenesulfanyl)-octanoic acid hydroxyamide was isolated as colorless solid. Yield: 99%, MP: 58 C; MS: 284(M-H).
  • 32
  • [ 371-42-6 ]
  • [ 90357-51-0 ]
  • [ 90357-06-5 ]
YieldReaction ConditionsOperation in experiment
97.3% A biphasic mixture of compound of formula 2 (10. Og, 0.037mole), 4-fluorothiophenol (4.33ml, 0.041mol), sodium hydroxide (0.74g, O.OI Smol), tetrabutylammonium hydrogen sulfate (1.88g, 5.5mmol), ethyl acetate (100ml) and water (20ml) was stirred at 25-300C for 3 hours. Potassium permanganate (17.54g, O. l l lmol) and water (80ml) was then added to the reaction mixture and stirring was continued for further 2.5 hours. A solution of sodium metabisulfite (45g) in water (90ml) was added to the reaction mixture and stirred at about 500C for 1 hour. The insoluble inorganic material was filtered, and the upper organic layer containing product was separated, The organic layer was washed sequentially with 2% HCl solution and water, concentrated and degassed under vacuum to obtain bicalutamide, 15.5g (97.3% yield). EPO <DP n="12"/>A suspension of bicalutamide (15.5g) in 2-propanol (100ml) was heated to reflux for 1 hour, and then gradually cooled to ambient temperature. The resultant slurry was filtered, washed with 2-propanol, and dried at about 5O0C to obtain bicalutamide of HPLC purity 99.16%.
  • 33
  • [ 371-42-6 ]
  • [ 7681-65-4 ]
  • [ 23616-57-1 ]
  • [ 633304-04-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In methanol; water; N,N-dimethyl-formamide; EXAMPLE 9 Preparation of 3-[(4-Fluorophenyl)thio]-1H-pyrrolo[2,3-b]pyridine A solution of <strong>[23616-57-1]3-iodo-1H-pyrrolo[2,3-b]pyridine</strong> (4.0 g, 16.4 mmol) in DMF is treated with 4-fluorobenzenethiol (2.09 mL, 19.7 mmol), potassium carbonate (3.40 g, 24.6 mmol), and copper iodide (4.21 g, 22.1 mmol). The reaction mixture is heated at 65 C. for 4 h, cooled, diluted with conc. aqueous NH4OH and extracted with ethyl acetate. The extracts are combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Chromatography (1:50 methanol:CH2Cl2) of the residue, followed by methanol/H2O crystallization affords the title compound as an off-white solid, 3.56 g, mp 183-184 C., characterized by mass spectral and NMR analyses.
  • 34
  • [ 18592-13-7 ]
  • [ 371-42-6 ]
  • [ 1009628-49-2 ]
YieldReaction ConditionsOperation in experiment
6-[(4-Fluorophenyl)sulfanylmethyl]-1H-pyrimidine-2,4-dione DBU (4.02 mL, 26.91 mmol) was added to 4-fluorobenzenethiol (3.45 g, 26.91 mmol), in DMF (90 mL) at RT. The resulting solution was stirred at 20 C. for 15 minutes. 6-(Chloromethyl)-1H-pyrimidine-2,4-dione (2.88 g, 17.94 mmol) was then added and the reaction stirred for 4 hours. The reaction mixture was concentrated and diluted with DCM (100 mL), and washed with water (100 mL). The aqueous layer was acidified with 2M hydrochloric acid to give a white solid which was filtered and washed with water then dried under vacuum to give desired product (2.5 g). NMR Spectrum: 1H NMR (400.132 MHz, DMSO-d6) delta 3.80 (2H, s), 5.20 (1H, s), 7.18-7.23 (2H, m), 7.45-7.49 (2H, m), 10.90 (1H, s), 10.93 (1H, s)
  • 35
  • [ 1860-99-7 ]
  • [ 371-42-6 ]
  • [ 71-36-3 ]
  • 3-dibutoxymethyl-2-(4-fluorobenzenesulphanyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride;tetrakis(triphenylphosphine) palladium(0); at 120℃; for 1.5h; A mixture of sodium hydride (60percent dispersion in mineral oil, 0.21 g) and n- butanol (10 ml.) was treated with 4-fluorobenzenethiol (0.67 g), and the resulting mixture was added to a mixture of <strong>[1860-99-7]2-bromothiophene-3-carbaldehyde</strong> (1.0 g), tetrakis(triphenylphosphine)palladium(0) (0.12 g) and pi-butanol (5.0 mL), and the resulting mixture was heated at 12O0C for 90 minutes. The mixture was partitioned between ethyl acetate and water and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by the column chromatography on silica gel, eluting with a mixture of cyclohexane and dichloromethane (3:1 to 1:2 by volume) to give 3- dibutoxymethyl-2-(4-fluorobenzenesulfonyl)thiophene (1.6 g) as a colourless oil.
  • 36
  • [ 1994-13-4 ]
  • [ 371-42-6 ]
  • [ 1159020-27-5 ]
  • 37
  • [ 371-42-6 ]
  • [ 90357-53-2 ]
  • [ 906008-93-3 ]
YieldReaction ConditionsOperation in experiment
50% General procedure: To a mixture of 60% sodiumhydride in mineral oil (94.43 mg, 2.36 mmol) in anhydrous tetrahydrofuran(5 mL) at 0 C under anhydrous THF under nitrogenatmosphere, was added dropwise the corresponding thiophenol10-13 (2.05 mmol). This mixture was stirred at room temperaturefor 20 min. A solution of the appropriate intermediate 6-9(1.57 mmol in 5mL anhydrous tetrahydrofuran) was added slowlyto the thiophenol mixture and stirred at room temperature for 24 h.The mixture was concentrated under vacuum then diluted withethyl acetate (30 mL), washed with brine (20 mL) and water(30 mL), dried over anhydrous sodium sulfate and concentratedunder vacuum. The crude residue was purified by column chromatographyeluting with chloroform-ethyl acetate graduallyincreasing from 95:5 to 90:10 v/v.
  • 38
  • [ 107-94-8 ]
  • [ 371-42-6 ]
  • [ 19543-85-2 ]
YieldReaction ConditionsOperation in experiment
94% A mixture (I) of 4-fluorothiophenol (10.75 g, 84mmol), potassium hydroxide (5.7 g, 87 mmol), ethanol (48 ml) and water (48 ml) were heated at 60C. To a solution of 30% potassium carbonate solution (60 ml) was added beta-<strong>[107-94-8]chloropropionic acid</strong> (9.07 g, 84 mmol). The mixture (II) was stirred at room temperature for 0.5 h. The mixture of (I) and (II) was reflux at 96C for 5 h. Then the mixture was cooled to room temperature and then the solution was added HCl to pH 2. The white solid was filtrated and the filter cake washed with water. After drying, compounds 5a (15.8 g, 94.0%) was obtained.
With potassium hydroxide; for 0.25h;Microwave irradiation; General procedure: Substituted thiophenol (0.1mol) and -chloropropionicacid (0.12mol) were placed in 250ml conical flask, and KOH(0.24mol) was added. The mixture was completely agitatedtill uniformity, and irradiated for 15min in microwave oven.After the reaction system was cooled to room temperature,the solution was adjusted by concentrated hydrochloric acidto pH 1. A large number of white precipitates occurred andthe resultant solution was filtrated. The obtained filter cakewas rinsed with water, and then recrystallized from ethanol/water. After drying, white solid compound 1 was obtained.Compound 1 was dissolved in concentrated sulfuricacid (1g: 4ml) and kept at room temperature for 12h and thenplaced in the ice water bath for dissociation. Solid precipitateproduced substituted thiochromanone 2
With sodium hydroxide; In water;Microwave irradiation; General procedure: 1:1.2:2.4 molar mixture of substituted benzenethiols (50mmol), 3-chloropropanoic acid (6.5g, 60mmol), and NaOH (4.8g, 120mmol) in 5mL water was irradiated under microwave irradiation for 5-6min, the reactant was cooled to ambient temperature and then HCl (1mol/L) was added to adjust the pH of solution below 2. Maintaining the temperature at C, a lot of white precipitate was created. The precipitate was filtered and washed with water.12 The dried white precipitate and a solution of concentrated sulfuric acid (40mL, 98%) were stirred sufficiently and then the reaction solution was mixed with ice water (100mL) after 12h at room temperature, the solid product formed was collected, washed with water and recrystallized from ethanol water solution (ethanol/H2O=8:2) (see Scheme 1).13,14
With potassium hydroxide; for 0.25h;Microwave irradiation; General procedure: 1.1.1 Synthetic method of substituted thiochroman-4-ones: Substituted thiophenol (0.1mol) and beta-<strong>[107-94-8]chloropropionic acid</strong> (0.12mol) were placed in 250 ml conical flask, and KOH (0.24mol) was added. The mixture was completely agitated till uniformity, and irradiated for 15min inmicrowave oven. After the reaction system was cooled to room temperature, the solution was adjusted by concentrated hydrochloric acid to pH 1. A large number of white precipitate occurred,the resultant solution was filtrated. The obtained filter cake was rinsed with a mass of water, and then recrystallized by ethanol/water. After drying, The compound was dissolved in four times thevolume concentrated sulfuric acid, kept at room temperature for 12 h and then placed in the icewater bath for dissociation. Solid precipitation substituted thiochromanone was obtained.
37.95 g With sodium hydroxide; In water; at 100℃; for 3h; General procedure: 24.80g (0.2mol) 4-fluorothiophenol, 19.20g (0.48mol) sodium hydroxide and 500mL water were placed in 1000ml conical flask, and 200 ml 26.04g (0.24mol) beta-<strong>[107-94-8]chloropropionic acid</strong> solution was dropwise added. After the dropwise addition, the system was reflux at 100C for 3h. After the reaction, the system was cooled to room temperature, and the solution was adjusted by dilute hydrochloric acid to pH 1. A large number of white precipitates were filtrated. The obtained filter cake was rinsed with a mass of water, and then recrystallized by ethanol:water (1:5, v/v). After drying, 37.95g white solid compound 2 was obtained.
With sodium carbonate; sodium hydroxide; In ethanol; water; at 20℃; for 1h;Reflux; General procedure: Thiophenols A were purchased from Fisher Scientific. To a 250 mL flask with a stirrer bar, was added 1MNaOH (25 mL), 1M Na2CO3 (25 mL). To this, thiophenols A (50 mmol) was added as ethanol solution (30mL) followed by the addition of 3-chloropropanoic acid (5.5 g, 151 mmol) in 20 mL water. The resultantreaction mixture was stirred at room temperature for 1 h, and then it was heated to reflux. When thereaction was completed as indicated by TLC monitor, the reaction mixture was cooled down to roomtemperature, then ethanol was evaporated under vacuum and then it was acidified to pH 1-2 with conc.HCl (18%). The solution was extracted with DCM for three times (3 X 30 mL) and the combined organiclayers were dried (Na2SO4), filtered, and concentrated under vacuum. The crude product was thenpurified by flash column chromatography (EtOAc/hexanes, 5% to 25%) to give 3-(phenylthio)propanoicacid B in 72- 85% yield.
In ethanol; water; at 20℃; for 2h;Reflux; Thiochromone were prepared according to previously reported procedures.Thiophenols were purchased and used as received. A250 mL flask was fitted with astirrer bar and charged with 1M NaOH (50 mL) and 1M Na2CO3 (50 mL). A solutionof thiophenols S1 (100mmol) in 60 mL EtOH and 3-chloropropanoic acid (11 g, 102mmol) in 40 mL H2O were added respectively to the above solution. The reactionmixture was stirred at room temperature for 2 h, and then temperature increased toreflux. After the reaction was completed as determined by TLC and cooled down toroom temperature, EtOH was evaporated and then the aqueous phase was acidified topH 1~2 with conc. HCl. The solution was extracted with CH2Cl2 for three times andthe combined organic layers were dried over anhydrous Na2SO4, filtered, andconcentrated. The residue was purified by flash column chromatography(hexane/EtOAc, 20/1 to 5/1) to produce 3-(phenylthio)propanoic acid S2 in 85-95%yield

  • 39
  • [ 371-42-6 ]
  • [ 13301-04-7 ]
  • [ 1093383-18-6 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h; To a dimethylformamide (160 ml) solution of <strong>[13301-04-7]3,6-dibromopyrazine-2-carboxylic acid methyl ester</strong> (4.0 g, 13.5 mmol), 4-fluorothiophenol(1.36 ml, 12.8 mmol)) and potassium carbonate (1.86 g, 13.5 mmol) were added and the mixture was stirred for 2 hours at room temperature. The reaction solution was poured into water, extracted with ethyl acetate and washed (with water and brine, in this order), dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: hexane: ethyl acetate = 20:1 to 10:1] to obtain 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester (1.62 g) in the form of colorless powder. MS (ESI/APCI Dual): 343 (M+1) 1H NMR (300 MHz, CDC13) delta ppm 4.06 (s, 3 H) 6.99 - 7.25 (m, 2 H) 7.41 - 7.59 (m, 2 H) 8.43 (s, 1 H)
  • 40
  • [ 371-42-6 ]
  • [ 13301-04-7 ]
  • [ 1093383-18-6 ]
  • [ 1093383-19-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h; To a dimethylformamide (15 ml) solution of <strong>[13301-04-7]3,6-dibromopyrazine-2-carboxylic acid methyl ester</strong> (see Patent Document: BE662507)(780 mg, 2.64 mmol), potassium carbonate (364 mg, 2.64 mmol)) and 4-fluorothiophenol (0.253 ml, 2.37 mmol) were sequentially added at room temperature and the mixture was stirred at room temperature for one hour. The reaction solution was charged with water, extracted with chloroform and then dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: chloroform hexane = 1:2 to 10:0] and purified by recycle preparative HPLC (LC-908 type, Japan Analytical Industry Co. , Ltd.) [developing eluent: chloroform] to obtain a mixture of 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester and 3-bromo-6-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester (940 mg) in the form of a light yellow solid substance.
  • 41
  • [ 371-42-6 ]
  • [ 13301-04-7 ]
  • [ 1093383-18-6 ]
  • [ 1093383-19-7 ]
  • [ 1093383-21-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 0.5h; To a dimethylformamide (300 ml) solution of <strong>[13301-04-7]3,6-dibromopyrazine-2-carboxylic acid methyl ester</strong> (7.47 g, 25.2 mmol), potassium carbonate (3.48 g, 25.2 mmol) and 4-fluorothiophenol (2.42 ml, 22.7 mmol) were sequentially added at room temperature and the mixture was stirred at room temperature for 30 minutes. The reaction solution was charged with water, extracted with ethyl acetate and then washed (with water and brine in this order). The water phases were combined and re-extracted with chloroform. The organic phases were combined, dried (over anhydrous magnesium sulfate), filtered and concentrated to obtain a residue, which was purified by silica gel column chromatography [developing eluent: hexane: ethyl acetate = 25:1 to 10:1] to obtain a mixture (9.29 g) of 6-bromo-3-[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester, 3-bromo-6-1(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester and 3,6-bis[(4-fluorophenyl)sulfanyl]pyrazine-2-carboxylic acid methyl ester.
  • 42
  • [ 371-42-6 ]
  • [ 715-11-7 ]
  • 4-fluoro-1-(1-methylpropylthio)benzene [ No CAS ]
  • 43
  • [ 371-42-6 ]
  • [ 13720-94-0 ]
  • ethyl 4-phenylthio-quinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; at 20℃; for 0.5h; Preparation Example 2Ethyl 4-substituted thiophenyl-quinoline-3-carboxylate (E14); A mixture of <strong>[13720-94-0]ethyl 4-chloro-quinoline-3-carboxylate</strong> (8.0 g, 34 mmol), 4-fluoro thiophenol (5.2 g, 41 mmol) and triethylamine (6.9 g, 68 mmol) in THF (80 mL) was stirred at room temperature for 30 min. The insoluble material was filtered off. The filtrate was concentrated, and the residue was recrystallized with toluene/petroleum ether to afford ethyl 4-(4-fluoro-thiophenyl-quinoline-3-carboxylate (10.0 g, E2). Ethyl 4-thiophenyl-quinoline-3-carboxylate (E1), ethyl 4-(3-methoxy-thiophenyl-quinoline-3-carboxylate (E3), and ethyl 4-(4-isopropyl-thiophenyl-quinoline-3-carboxylate (E4), were prepared in the manner analogous to the method described above, when 4-fluoro-thiophenol was replaced with thiophenol, 3-methoxy-thiophenol, and 4-isopropyl-thiophenol respectively. The data of yield, melting points (Mp.) and 1H-NMR spectra of compound E1-4 was shown in FIG. 1A, FIG. 1B.
  • 44
  • [ 371-42-6 ]
  • [ 71838-16-9 ]
  • [ 1293343-28-8 ]
  • 46
  • [ 371-42-6 ]
  • [ 368-88-7 ]
  • 47
  • [ 371-42-6 ]
  • [ 90357-51-0 ]
  • N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(p-tolylthio)propanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.2% Charged SOL of Acetone and 5kg of N-[4-cyano-3-(trifluoromethyl) phenyl] 2-Methyloxirane- 2-carboxamide (1) into a SS reactor at room temperature under stirring and stirred till to obtain the clear solution. 1.96 kg of Potassium Carbonate was added under stirring and cooled the reaction mixture to 10-15C under stirring.Added 3.0 kg 4-Fluorothiophenol slowly through addition tank in 3-4 hours at 10-15 C under stirring. Removed the cooling and brought the reaction mixture to RT under stirring and stirred for 5-6 hours at RT while monitoring the reaction by HPLC for the presence of unreacted - N-[4-cyano-3-(trifluoro methyl) phenyl] 2-Methyloxirane-2-carboxamide (1) ( unreacted compound (1) < 0.50%].Filter the reaction mixture over Nutsche Filter and wash with 10L acetone. Acetone was later on recovered completely at 40-50C under vacuum until dryness. To this dried residue, 50L DM water was added and stirred the solution for 4-5 hours at RT. About 25 L Toluene was added to this solution and stirred the reaction mixture for 10-12 hours. (Solid become free flowing in nature). The reaction mixture was filtered and washed with 10L Toluene. The solid was dried for 6-7 hours under vacuum at 40-50C 7.0kg solid was obtained ; Yield - 95.2%, Water content < 0.5% w/w; Purity > 99.0% by HPLC.
  • 48
  • [ 368-88-7 ]
  • [ 371-42-6 ]
  • 49
  • [ 402-46-0 ]
  • [ 371-42-6 ]
  • 50
  • [ 19070-16-7 ]
  • [ 82104-74-3 ]
  • [ 371-42-6 ]
  • [ 352-13-6 ]
  • [ 1448549-70-9 ]
YieldReaction ConditionsOperation in experiment
4-Fluorophenyl magnesium bromide (86mL 1.1M solution in THF, 94mmol) was added dropwise to 5-cyano-3H-isobenzofuran-l-one (15g, 94mmol) in 150mL THF at 0-5°C to give solution A. 4-Fluorophenyl magnesium bromide (188mL 1.0M solution in THF, 180mmol) was added dropwise to 4-fluorothiophenol (24.2g, 188mmol) in lOOmL THF at 0-5°C. 155mL of the resulting solution was added to solution A from above at 0-5°C. The reaction mixture was stirred at room temperature overnight and cooled to 0-5°C. N-(Dimethyl)-propyl-l- magnesiumchloride (79mL 1.2M solution in THF, 94mmol) was added. 100 mL saturated aqueous ammonium chloride was added. The mixture was filtrated and the two phases were separated. The aqueous phase was extracted with lOOmL ethyl acetate and 50mL toluene. The combined organic phases were extracted with 2 x IN H2SO4 (aq). The organic phase was concentrated in vacuo and toluene and isopropyl acetate were added. The organic phase was extracted with 2 x IN H2SO4 (aq). The combined H2SO4 phases were basified with concentrated aqueous ammonia and extracted with toluene. 2N HCl (aq) (40mL) was added to the organic phase at room temperature. The mixture was stirred at room temperature overnight. A solid was formed. The solid was reprecipitated from 50mL isopropyl acetate. The solid was washed with diethyl ether to give the intermediate of general structure III. The intermediate III Rl=cyano, R2=4-(4-fluoro-phenylsulfanyl)-phenyl was ring-closed analogously to the method described for example 1. (l-(3-dimethylamino-propyl)-l- naphthalen-l-yl-l,3-dihydro-isobenzofuran-5-carbonitrile). The title compound was isolated as the oxalate salt.
  • 51
  • [ 82104-74-3 ]
  • [ 371-42-6 ]
  • [ 352-13-6 ]
  • [ 1448549-68-5 ]
YieldReaction ConditionsOperation in experiment
21.2 g Grignard Reaction Mixture: To a stirred solution/suspension of 5-cyanophthalide (15 g, 94.2 mmol), THF (250 mL), and magnesium bromide di ethyl etherate (6.08 g, 23.6 mmol) under nitrogen and with mechanical stirring at 0 °C was added dropwise a solution of 4- fluorophenylmagnesium bromide in THF ( 0.85 M) until less than 5 percent of the 5- cyanophthalide remained (ca. 120 mL). In a separate flask, to a stirred suspension of sodium hydride (5.65 g, 236 mmol) in THF (50 mL) was added dropwise a solution of 4-fluorothiophenol (24.2 g, 188 mmol) in THF (50 mL) with cooling using a water bath. After the exothermic addition was complete, the resultant solution was stirred for 1 h at 25 °C. This solution was then added dropwise to the Grignard Reaction Mixture at 0 °C, and was allowed to stir at 25 °C overnight. The mixture was cooled to 10-15 °C, and water (200 mL) was added dropwise. Sodium borohydride (1.78 g, 47.1 mmol) was added neat in 5 portions, and the mixture was stirred at 25 °C until analysis by HPLC indicated that the reduction was complete. The pH of the mixture was adjusted to 3-5 by the addition of aqueous hydrochloric acid (4 M). The organic phase was then separated by decantation due to the thickness of the aqueous phase. The aqueous phase was extracted with isopropyl acetate (200 mL) and the organic phases were combined and evaporated under reduced pressure. The residue was dissolved in isopropyl acetate (200 mL) and was washed with water (100 mL) and an aqueous solution of sodium hydroxide (1.0 M, 100 mL). The organic phase was dried over anhydrous magnesium sulphate and evaporated under reduced pressure to give an oil (48 g). HPLC analysis indicated a purity of 46 percent. This oil was dissolved by heating in toluene (140 mL) at reflux, and then was allowed to cool to 25 °C over 1 h. The solid formed was removed by filtration, washed with toluene (2 x 20 mL) and dried under vacuum (40 °C) to give 21.2 g (purity 98.9 percent by HPLC) of the title compound.
  • 52
  • [ 371-42-6 ]
  • [ 68-12-2 ]
  • [ 383-31-3 ]
  • 53
  • [ 371-42-6 ]
  • [ 626-00-6 ]
  • [ 1520092-66-3 ]
YieldReaction ConditionsOperation in experiment
71% With copper(l) iodide; 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone; caesium carbonate; In dimethyl sulfoxide; at 100℃; for 18h;Inert atmosphere; General procedure: Diiodobenzene 1 (0.2 mmol), (het)aryl thiol 2 (0.3 mmol), CuI (0.04mmol), ligand L1 (0.04 mmol), and Cs2CO3 (0.4 mmol) were added to DMSO (1 mL) in a 25-mL round-bottomed flask equipped witha stirring bar. The mixture was stirred at 100 C for 18 h under N2 then cooled to r.t. H2O (8 mL) was added and the resulting residue was extracted with EtOAc (3 × 8 mL). The organic layers were combined, dried (MgSO4), and concentrated under reduced pressure.The residue was purified by silica flash column chromatography (petroleum ether).
  • 54
  • [ 371-42-6 ]
  • [ 146137-79-3 ]
  • [ 1613335-09-3 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 18h; 3-formyl-4-(4-fluorophenylthio)benzonitrile In a 50 mL round-bottomed flask, <strong>[146137-79-3]4-fluoro-3-formylbenzonitrile</strong> (900 mg, 5.73 mmol) and potassium carbonate (872 mg, 6.31 mmol) were suspended in DMF (10 mL) to give a yellow suspension. Then 4-fluorobenzenethiol (0.654 mL, 6.02 mmol) was added and the reaction mixture heated at 70°C for 18h. The reaction mixture was poured into water. The solid was filtered, washed with water and with a few amount of DIPE then dried in vacuo to give 1.44g of a pale yellow solid (Yield : 97percent) APCI-MS: (M+H)+ =257 1H NMR (300 MHz, DMSO-d6) delta ppm: 10.12 (s, 1H), 8.49 (d, J = 1.9 Hz, 1H), 7.85 (dd, J = 8.5, 2.0 Hz, 1H), 7.71 - 7.62 (m, 2H), 7.43 (ddd, J = 10.9, 6.0, 2.6 Hz, 2H), 6.80 (d, J = 8.5 Hz, 1H).
  • 55
  • [ 371-42-6 ]
  • [ 114077-82-6 ]
  • [ 1613335-25-3 ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 1h; 4-fluorophenylthio-3-formylpyridine A mixture of <strong>[114077-82-6]4-chloronicotinaldehyde</strong> (500 mg, 3.53 mmol), potassium carbonate (537 mg, 3.89 mmol) and 4-fluorobenzenethiol (0.403 mL, 3.71 mmol) in DMF (10 mL) was heated at 70C for lh. The reaction mixture was quenched with water, extracted with 3 x 20 mL of AcOEt, the combined organic were washed with brine, dried over Na2S04, filtered and concentrated under vacuum to give a brown oil. The oil was triturated with 5 mL of DIPE to give 0.46 g of a beige solid (Yield: 55%). APCI-MS: (M+H)+ =234 1H NMR (300 MHz, DMSO-d6) delta ppm: 10.19 (s, 1H), 9.03 (s, 1H), 8.45 (d, J = 5.6 Hz, 1H), 7.69 (dd, J = 8.5, 5.5 Hz, 2H), 7.45 (t, J = 8.7 Hz, 2H), 6.61 (d, J = 5.6 Hz, 1H).
  • 56
  • [ 371-42-6 ]
  • [ 27317-69-7 ]
  • [ 1620161-74-1 ]
  • 57
  • [ 371-42-6 ]
  • [ 4489-34-3 ]
  • C22H13F3N2S3 [ No CAS ]
  • 59
  • [ 371-42-6 ]
  • [ 374930-88-8 ]
  • tert-butyl 4-(5-(4-fluorophenylthio)pyrimidin-2-yl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere; A stirred solution of <strong>[374930-88-8]tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate</strong> (1 g, 2.924 mmol), 4-fluorobenzenethiol (561 mg, 4.386 mmol), Pd2(dba)3 (267 mg, 0.292 mmol), Xantphos (169 mg, 0.292 mmol) and DIPEA (754 mg, 5.848 mmol) in dioxane (50 mL) was degassed with nitrogen for three times, and then heated at 110 C. for 16 hrs. The reaction mixture was cooled to RT and concentrated under reduced pressure to give a residue, which was purified by flash chromatography (silica gel, 0-20% EtOAc/PE) to afford the title compound as a white solid. (500 mg, yield 44%, purity: 99%). MS (ES+) C19H23FN4O2S requires: 390. found 391 [M+H]+.
  • 60
  • [ 371-42-6 ]
  • [ 406207-65-6 ]
  • C17H17FN2S [ No CAS ]
  • 61
  • [ 371-42-6 ]
  • [ 874-10-2 ]
  • C14H11FN2S [ No CAS ]
  • 62
  • [ 371-42-6 ]
  • [ 874-38-4 ]
  • 3-((4-fluorophenyl)thio)-6-methylimidazo[1,2-a]pyridine [ No CAS ]
  • 63
  • [ 371-42-6 ]
  • [ 20358-07-0 ]
  • 64
  • [ 371-42-6 ]
  • [ 41602-56-6 ]
  • [ 109-77-3 ]
  • 2,4-diamino-8-(dimethylamino)-5-((4-fluorophenyl)thio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine; In ethanol; for 4h;Reflux; General procedure: An amount of malonitrile (2 mmol), desired thiophenol (1 mmol) and triethyl amine (0.1 mmol) were added in a solution of 4-dimethylamino-salisaldehyde (1 mmol) in 7 mL EtOH. The resulting mixture was allowed to reflux over 4 h, at which point the product precipitates out of the solution. The resulting precipitate was filtered off and dried under vacuum. The residue was then dissolved in 3 mL DMF. The insoluble particles were filtered off. A volume of 4 mL H2O was then poured into the resulting filtrate, leading to the precipitation of the pure product out of the solution. The precipitates were filtered off and dried under vacuum, leading to the pure 5H-substituted-thiochromenopyridines (1g-1i, 89%-91%) as light pinkish solids.
  • 65
  • [ 4208-49-5 ]
  • [ 371-42-6 ]
  • [ 405-31-2 ]
  • C14H13FO3S [ No CAS ]
  • 67
  • [ 371-42-6 ]
  • [ 824-80-6 ]
  • [ 2905-15-9 ]
YieldReaction ConditionsOperation in experiment
92% With iron(III) chloride; In N,N-dimethyl-formamide; at 20℃; for 0.75h;Green chemistry; General procedure: A mixture of the appropriate thiol 1 (0.5 mmol), sodium thiosulfinate 2 (1.0 mmol), and FeCl3 (20 mol%) in DMF (3 mL) was stirred at r.t. for 30-60 min under air in a round-bottomed flask.When the reaction was complete (TLC), H2O (5 mL) was added and the mixture was extracted with EtOAc (3 × 5 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using a gradient mixture of hexane and EtOAc as eluent
  • 69
  • [ 371-42-6 ]
  • [ 870997-85-6 ]
  • 3-amino-5-(4-fluorophenylsulfanyl)pyridine-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 5.0h; Step 1: 3-amino-5-((4-fluorophenyl)thio)picolinic acid 3-Amino-5-bromopicolinic acid (5 g, 23.04 mmol) was stirred in N,N-dimethylformamide (50 mL). 4-Fluorobenzenethiol (3.54 g, 27.6 mmol) and N,N-diisopropylethylamine (8.05 mL, 46.1 mmol) were added. The reaction mixture was heated at 100 C. for 5 hours. The mixture was cooled to room temperature. The reaction mixture was slowly poured into ice water, and the pH was adjusted to 5 with 1N aqueous HCl solution. The solid was filtered and washed with cold water, followed by petroleum ether, to give the titled compound (5.6 g, 20.77 mmol, 90% yield); MS (ESI+) m/z 265.7 (M+H)+.
In N,N-dimethyl acetamide; at 140℃; for 0.833333h;Microwave irradiation; A solution of <strong>[870997-85-6]3-amino-5-bromopyridine-2-carboxylic acid</strong> (Int 1, 13 g, 60 mmol), 4- fluoro-benzenethiol (CAS: 371-42-6, 7.68 g, 60 mmol) and DBU (0.89 mL, 6 mmol) was prepared in DMA (90 mL). This mixture was heated at 140 C for 50 minutes in the microwave reactor. Next, the mixture was diluted with a mixture of 1% AcOH in water. A suspension was obtained that was subsequently filtered. The collected solid was washed with 1% AcOH in water followed by washing with petroleum ether. After drying in a vacuum oven, the titled compound was obtained.
  • 70
  • [ 371-42-6 ]
  • [ 381-98-6 ]
  • 6-fluoro-3-(trifluoromethyl)thiochroman-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With trifluorormethanesulfonic acid; In dichloromethane; at 20 - 110℃; for 0.583333h;Inert atmosphere; Microwave irradiation; General procedure: 2-trifluoromethylacrylic acid 2d (1.3 mmol, 182 mg) was transferred into a microwave vial with and a magnetic stir bar. 0.5 mL of dry CH2Cl2 was added to dissolve (partially) the acid. The solution was degassed with argon and cooled in an ice bath before the addition of the thiol (1, 1mmol). To the cooled reaction mixture 1.5 mL of CF3SO3H was added dropwise under argon atmosphere and the vial was sealed. The reaction was allowed to stir at room temperature for 30 minutes and subsequently subjected to microwave heating at 110 C for 5 minutes. After the reaction was completed, the reaction mixture was poured onto crushed ice and was quenched with solid NaHCO3. The quenched reaction mixture was extracted three times with CH2Cl2 and the combined organic extract was washed with aqueous NaHCO3 and water. The organic layer was dried over Na2SO4 and concentrated in vacuo to yield the crude product. Colored impurities were removed by addiction of activated charcoal followed by filtration. Further purification by column chromatography (hexanes/ethyl acetate) yielded the pure 3-(trifluoromethyl)thio-chroman-4-one (5).
  • 72
  • [ 371-42-6 ]
  • [ 13035-61-5 ]
  • 4-fluorobenzene 2,3,5-tetra-O-acetyl-1-thio-β-D-ribofuranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With indium(III) bromide; In dichloromethane; at 20℃; for 2h; General procedure: To a solution of beta-ribofuranosetetraacetate (0.1 mmol) and 4-fluorobenzenethiol (0.12 mmol)in CH2Cl2 (2 mL) was added InBr3 (0.01 mmol) and the reactionmixture was stirred for 2 h at room temperature. Upon completionof the reaction (monitored by TLC), the reaction mixturewas concentrated under reduced pressure and the resultingresidue was subjected to flash chromatograph (petroleumether-EtOAc, 4:1) to afford the desired product 1j. Yield: 98%;colorless oil. 1H NMR (400 MHz, CDCl3): delta = 7.52 (dd, J = 8.8,5.2 Hz, 2 H), 7.04 (t, J = 8.7 Hz, 2 H), 5.18-5.24 (m, 3 H), 4.23-4.29 (m, 2 H), 4.10 (dd, J = 12.8, 5.4 Hz, 1 H), 2.11 (s, 3 H), 2.08(s, 3 H), 2.05 (s, 3 H). 13C NMR (100 MHz, CDCl3): delta = 170.4,169.5, 169.3, 164.4, 161.9, 136.3, 126.3, 116.1, 88.0, 80.1, 73.6,71.3, 63.3, 20.7, 20.5. HRMS (ESI): m/z [M +H]+ calcd forC17H20FO7S: 387.0914; found: 387.0917.
  • 73
  • [ 371-42-6 ]
  • [ 4049-33-6 ]
  • 4-fluorobenzene 2,3,4-tri-O-acetyl-1-thio-β-D-xylopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With indium(III) bromide; In dichloromethane; at 20℃; for 2h; General procedure: To a solution of peracetylated aldose (0.1mmol) in CH2Cl2 (2 mL) were added thiophenolor selenophenol (0.12mmol) and InBr3 (3mg, 0.01mol). The reaction mixture was allowedto stir for 2 h at room temperature. After completion as monitored by TLC, the reactionmixture was concentrated. The resultant residue was subjected to flash chromatograph togive the goal products.
  • 74
  • [ 371-42-6 ]
  • [ 90357-53-2 ]
  • [ 90357-06-5 ]
YieldReaction ConditionsOperation in experiment
88% 2.540 g (10 mmol) of N- (4-cyano-3- (trifluoromethyl) phenyl) methacrylamide and1.962 g (15 mmol) of p-fluorobenzenethiol,Dissolved in 100 ml of acetonitrile, in an oxygen atmosphere,45 under the conditions of stirring 10h;Subsequently, 15.636 g of potassium persulfate complex salt (4.5% active oxygen) was added to the reaction system,Continue stirring 18h;After the reaction was filtered, the mother liquor was distilled off under reduced pressure to conduct column chromatography (developing system petroleum ether: ethyl acetate = 4: 1 v v)Pure white bicalutamide obtained, its nuclear magnetic hydrogen spectrum shown in Figure 1. Yield 88%
  • 75
  • [ 371-42-6 ]
  • [ 1064194-10-0 ]
  • tert-butyl 3-[(4-fluorophenyl)thio]azetidine-1-carboxylate [ No CAS ]
  • 76
  • [ 340825-13-0 ]
  • [ 371-42-6 ]
  • (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane [ No CAS ]
  • (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; at 20℃;Cooling with ice; Alternative Procedure: A solution of <strong>[340825-13-0]6-iodo-3,4-dihydronaphthalen-1(2H)-one</strong> (5.0 g, 18.4 mmol), 4-fluorobenzenethiol (4.1 mL, 38.6 mmol) and absolute ethanol (20 mL) was cooled on an ice-water bath and bubbled with HCl gas until saturation was reached (observed by the formation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in diethyl ether (250 mL) and washed sequentially with water (2*125 mL), 0.5 M aqueous Na2CO3 (3*100 mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.20 g) which was a mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane). The solid was dissolved in chloroform (150 mL) and cooled in an ice-water bath. A solution of mCPBA (35.0 g, 156 mmol) in DCM (200 mL) was washed with brine (50 mL), dried over Na2SO4, filtered, and the filter cake was washed with DCM (50 mL). The combined filtrates were added dropwise in portions to the chloroform solution of the mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) until the reaction was completed as judged by LCMS (175 mL of the mCPBA solution was needed). The mixture was cooled in an ice bath, filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueous Na2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2*120 mL), 10% aqueous Na2CO3 (3*200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4-fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white amorphous solid.
  • 77
  • [ 340825-13-0 ]
  • [ 371-42-6 ]
  • 4-((4-fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Alternative Procedure: A solution of <strong>[340825-13-0]6-iodo-3,4-dihydronaphthalen-1(2H)-one</strong> (5.0 g, 18.4 mmol), 4-fluorobenzenethiol (4.1 mL, 38.6 mmol) and absolute ethanol (20 mL) was cooled on an ice-water bath and bubbled with HCl gas until saturation was reached (observed by the formation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in diethyl ether (250 mL) and washed sequentially with water (2*125 mL), 0.5 M aqueous Na2CO3 (3*100 mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.20 g) which was a mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane). The solid was dissolved in chloroform (150 mL) and cooled in an ice-water bath. A solution of mCPBA (35.0 g, 156 mmol) in DCM (200 mL) was washed with brine (50 mL), dried over Na2SO4, filtered, and the filter cake was washed with DCM (50 mL). The combined filtrates were added dropwise in portions to the chloroform solution of the mixture of (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane and (6-iodo-1,2,3,4-tetrahydronaphthalene-1,1-diyl)bis((4-fluorophenyl)sulfane) until the reaction was completed as judged by LCMS (175 mL of the mCPBA solution was needed). The mixture was cooled in an ice bath, filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueous Na2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2*120 mL), 10% aqueous Na2CO3 (3*200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4-fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white amorphous solid.
  • 78
  • [ 371-42-6 ]
  • [ 2243-53-0 ]
  • trans-4-((4-fluorophenyl)thio)-5-phenyldihydrofuran-2(3H)-one [ No CAS ]
  • 4-((4-fluorophenyl)thio)-5-phenyldihydrofuran-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; In 1,2-dichloro-ethane; at 20℃; for 1.5h;Irradiation; General procedure: To a dried 30 ml vial equipped with a magnetic stir bar was added <strong>[2243-53-0]4-phenyl-but-3-enoic acid</strong> (1.0 mmol), thiophenol (2 mmol), 9-Mesityl-10-methyl acridinium tetrafluoroborate (2.0 mol %) in dichloroethane. The reaction was irradiated under Blue LED (= 450-495 nm) at room temperature for a period of 1.5-2.5 hours. After completion of reaction, as monitored by TLC, the crude reaction mixture was washed with NaHCO3 solutions and then extracted with ethyl acetate (3×10 mL). The organic layer was concentrated in vacou and the mixture was purified by silica gel column chromatography using EtOAc/Hexane (1:9) as eluent to afford pure product. Note: The reaction returns better yields without work up and can be directly loaded on the column for chromatography.
  • 79
  • [ 371-42-6 ]
  • [ 904929-24-4 ]
  • 3-bromo-7,8-bis((4-fluorophenyl)thio)-5,6,7,8-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In isopropyl alcohol; at 20℃; for 20.25h;Cooling with ice; A suspension of <strong>[904929-24-4]3-bromo-6,7-dihydroquinolin-8(5H)-one</strong> (5.58 g, 24.7 mmol) in IPA (49.4 mL) was treated with 4-fluorobenzenethiol (6.05 mL, 56.8 mmol). The solution was cooled in an ice-water bath and bubbled with HCl gas for about 5 min, and the resulting mixture (a suspension) was allowed to warm to rt overnight. After 17 h, significant starting material remained by LCMS. Additional IPA (49.4 mL) was added and the mixture was again bubbled with HCl gas for 10 min. After 3 h more, the mixture was poured into an ice-water mixture, EtOAc was added, and solid NaHCO3 was slowly added with stirring until gas evolution ceased. The organic phase was separated, washed sequentially with saturated aqueous NaHCO3 and brine, dried and concentrated to provide a yellow syrup. This was subjected to column chromatography to provide impure 3- bromo-7,8-bis((4-fluorophenyl)thio)-5,6,7,8-tetrahydroquinoline a light yellow syrup (3.67 g, 32% yield, about 80% purity), used without further purification. LCMS m/z 463.9, 465.9 (M+H)+, HPLC tR 1.24 min (method A).1H NMR (400 MHz, CDCl3) delta 8.58 (d, J=2.2 Hz, 1H), 7.65 (d, J=2.0 Hz, 1H), 7.32 - 7.25 (m, 2H), 7.14 (t, J=6.3 Hz, 2H), 6.98 - 6.90 (m, 4H), 4.41 (s, 1H), 3.64 - 3.59 (m, 1H), 3.05 (m, 1H), 2.87 - 2.68 (m, 2H), 2.11 - 2.03 (m, 1H).
  • 80
  • [ 340825-13-0 ]
  • [ 371-42-6 ]
  • (4-fluorophenyl)(6-iodo-3,4-dihydronaphthalen-1-yl)sulfane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In ethanol; water; at 20℃;Cooling with ice; A solution of 6-iodo-3,4-dihydronaphthalen-1(2B)-one (5.0 g, 18.38 minol), 4- fluorobenzenethiol (4.11 mL, 38.6 minol) and absolute ethanol (20 mL) was cooled with an ice-water bath and bubbled with HC1 gas until saturation was reached (observed by theformation of a white precipitate). The mixture was allowed to warm to rt and stirred overnight. The mixture was dissolved in ether (250 mL) and washed sequentially with water (2 x 125 mL), 0.5 M aqueous Na2CO3 (3 xlOO mL) and brine (100 mL). The organic layer was dried and concentrated to provide a solid (9.2 g) which was a mixture of thioketal and vinyl sulfide. The solid was dissolved in chloroform (150 mL) andcooled in an ice-water bath. A solution of mCPBA (35 g, 156 minol) in DCM (200 mL)was washed with brine (50 mL), dried, filtered, and the filter cake was washed with DCM(50 mL). The combined filtrates were added dropwise in portions to the chloroformsolution of the products from above until the reaction was completed as judged by LCMS(175 ml. of the mCPBA solution was needed). The mixture was cooled in an ice bath,filtered to remove the insoluble material, and the filtrate was stirred with 10% aqueousNa2S2O3 (120 mL) for 5 min. The organic phase was separated, washed sequentially with 10% aqueous Na2S2O3 (2 x 120 mL), 10% aqueous Na2CO3 (3 x 200 mL) and brine (150 mL), dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-20%) to give 4-((4- fluorophenyl)sulfonyl)-7-iodo-1,2-dihydronaphthalene (5.3 g, 70% yield) as a white foamy solid.
  • 81
  • [ 371-42-6 ]
  • [ 3747-74-8 ]
  • [ 1766-38-7 ]
  • 82
  • [ 1122-10-7 ]
  • [ 371-42-6 ]
  • 3,4-bis((4-fluorophenyl)thio)-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine; In tetrahydrofuran; at 20℃; for 1h; General procedure: To the solution of <strong>[1122-10-7]dibromomaleimide</strong> 1a orN-methyl<strong>[1122-10-7]dibromomaleimide</strong> 1b (1 mmol) in THF (20 ml)was added solution of the thiophenol (2.2 mmol) and triethylamine(2.2 mmol) in one portion. The resulting solutionwas stirred at room temperature for 1 h, then evaporated invacuo and the residue was redissolved in ethyl acetate-water(20 + 20 ml) mixture. The organic layer was separated,washed with aq. NaHCO3, dried over anhydrous Na2SO4and evaporated. The residue was purified by flash chromatography(ethyl acetate: petroleum ether 3:1).
  • 83
  • [ 371-42-6 ]
  • [ 6921-66-0 ]
  • 6-chloro-2,2-bis((4-fluorophenyl)thio)benzofuran-3(2H)-one [ No CAS ]
  • 84
  • [ 371-42-6 ]
  • [ 35120-18-4 ]
  • C13H15FO2S [ No CAS ]
  • 85
  • [ 371-42-6 ]
  • [ 71838-16-9 ]
  • C13H10BrFOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; oxygen; caesium carbonate; In dimethyl sulfoxide; at 95℃; for 4h;Schlenk technique; General procedure: To a solution of benzenethiol (0.6 mmol) in DMSO (2 mL) was added in a Schlenk tube at room temperature under oxygen condition. Subsequently, Cs2CO3 (1.0 mmol), CuI (0.02 mmol) and 1-bromo-2-iodobenzene (0.5 mmol) were added. The mixture was heated under 95 C for 4 h. After the reaction was completed, cooled to room temperature. Water (10 mL) was added to the reaction mixture and CH2Cl2 (3x10 mL) were used to extract the crude product. After removing the solvent, the resulting crude was purified by column chromatography with pure petroleum as eluent to give 1 as Colorless oily liquid.
  • 86
  • [ 371-42-6 ]
  • [ 71838-16-9 ]
  • 3-fluoro-7-methylphenoxathiine [ No CAS ]
  • 87
  • [ 18442-22-3 ]
  • [ 371-42-6 ]
  • C21H15BrF2OS2 [ No CAS ]
  • 88
  • [ 1753-75-9 ]
  • [ 371-42-6 ]
  • C12H7FN2S2 [ No CAS ]
  • 89
  • [ 371-42-6 ]
  • [ 84905-80-6 ]
  • C12H8FN3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 20℃; for 16h; General procedure: To a solution of 1-chloroisoquinoline 1a (2g, 12.225 mmol) in ethanol was added 4-fluorobenzenethiol 2a (1.436 mL, 13.447 mmol). The reaction was stirred at roomtemperature for 16h. The mixture was concentrated in vacuo. The crude waspurified by silica gel column chromatography using ethyl acetate/hexane to yieldpure compound (686 mg, 22%);
  • 90
  • [ 107-94-8 ]
  • [ 371-42-6 ]
  • [ 21243-18-5 ]
  • 91
  • [ 63224-42-0 ]
  • [ 371-42-6 ]
  • 4,7-bis((4-fluorophenyl)thio)-2,1,3-benzoselenadiazole [ No CAS ]
  • 92
  • [ 371-42-6 ]
  • [ 28122-13-6 ]
  • 93
  • [ 371-42-6 ]
  • [ 1611-83-2 ]
  • 3-[(4-fluorophenyl)thio]-2-hydroxy-2-methyl-N-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With air; In dimethyl sulfoxide; at 30℃; for 16h;Sealed tube; Schlenk technique; General procedure: A mixture of amide 1 (0.2 mmol), thiophenol derivative 2 (0.3 mmol), and DMSO (2 mL) was added to a 25 mL flame-dried Young-type tube under air atmosphere, and then the tube was sealed and the contents were stirred at 30 C for the indicated reaction time (Schemes 2 and 3). After evaporation of the solvent under reduced pressure, the residue was purified by flash column chromatography on silica gel to give the desired product 3.
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