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Structure of 696-63-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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C (sp3)-heteroatom bond formation by iron-catalyzed soft couplings
Semenya, Julius ; Yang, Yuanjie ; Lee, Hye Joon ; Giannantonio, Kimberly A ; Manduva, Rikhil ; Picazo, Elias
Abstract: Carbon-heteroatom bonds are of great importance due to their prevalence in pharmaceuticals, agrochemicals, materials, and natural products. Despite the effective use of metal-catalyzed crosscoupling reactions between sp2-hybridized organohalides and soft heteroatomic nucleophiles for carbon-heteroatom bond formation, the use of sp3-hybridized organohalides remain limited and the coupling with thiols remains elusive. Here, we report the coupling of sp3-hybridized benzyl or tertiary halides with soft thiol nucleophiles catalyzed by iron and extend the utility to alcohol and amine nucleophiles. The reaction is broad in substrate scope for both coupling partners and applicable in the construction of congested tri- and tetrasubstituted carbon centers as well as β-quaternary heteroatomic products. The synthetic utility is further emphasized by gram-scale synthesis and rapid herbicide library synthesis. Overall, we provide an efficient method to prepare pharmaceutically and materially relevant carbon-heteroatom bonds by expanding iron-catalyzed cross-coupling reactions to the coupling of sp3-hybridized organohalides with soft nucleophiles.
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Purchased from AmBeed: 76041-72-0 ; 2564-83-2 ; 73018-10-7 ; 63295-48-7 ; 1564-64-3 ; 65130-46-3 ; 15687-27-1 ; 91-60-1 ; 59163-91-6 ; 15570-12-4 ; 56673-34-8 ; 7217-59-6 ; 696-63-9
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CAS No. : | 696-63-9 |
Formula : | C7H8OS |
M.W : | 140.20 |
SMILES Code : | SC1=CC=C(OC)C=C1 |
MDL No. : | MFCD00004849 |
InChI Key : | NIFAOMSJMGEFTQ-UHFFFAOYSA-N |
Pubchem ID : | 12765 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H315-H318-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 |
Class: | 9 |
UN#: | 3334 |
Packing Group: | Ⅲ |
Num. heavy atoms | 9 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 40.19 |
TPSA ? Topological Polar Surface Area: Calculated from |
48.03 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.78 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.98 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.07 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.12 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.26 |
Solubility | 0.774 mg/ml ; 0.00552 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.41 |
Solubility | 0.549 mg/ml ; 0.00392 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.61 |
Solubility | 0.346 mg/ml ; 0.00247 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.89 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.02 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25 g | With copper; potassium hydroxide; In water; for 9h;Reflux; | 1) Synthesis of 5-chloro-2-(4-methoxyphenylthio)<strong>[13421-00-6]benzoic acid</strong> (Reference Example compound 1-1) [0170] <strong>[13421-00-6]5-chloro-2-iodo<strong>[13421-00-6]benzoic acid</strong></strong> (25.0 g), 4-methoxybenzenethiol (10.9 mL), potassium hydroxide (19.3 g), copper powder (0.60 g) and water (300 ml) was stirred under reflux for 9 hr. The reaction mixture was poured into a mixed solution of ethyl acetate and water, the aqueous layer was acidified with concentrated hydrochloric acid with stirring, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with diisopropyl ether and hexane (1:10) to give Reference Example compound 1-1 (25.0 g) as a white powder. 1H-NMR (CDCl3) delta (ppm) : 3.87 (3H, s), 6.69 (1H, d, J = 8.7 Hz), 6.99 (2H, d, J = 8.8 Hz), 7.23 (1H, dd, J = 2.6, 9.0 Hz), 7.49 (2H, d, J = 8.8 Hz), 8.09 (1H, d, J = 2.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | A solution of EtONa was prepared by dissolving Na (2.3g) in absolute EtOH (250 ml). Starting material 18-1 (14 g, 0.1 mol) was added drop wise to the solution of EtONa (0.1 mol). After stirring the at rt for 1 hour Starting material 18-2 (12.2 g, 0.1 mol) was added in one portion and the reaction mixture was brought to reflux and stirred under reflux for 3 hours. After cooling to rt, the reaction mixture was concentrated in vacuo and the residue was triturated with water (250 ml) followed by extraction with diethyl ether (4x125 mL). Combined organic layer was washed water (2x150 mL), brine (2x150 mL) and dried over Na2SO4, filtered and evaporated in vacuo to give Intermediate 18-3 which was used without further purification (22 g, 95%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With potassium carbonate; In acetone; for 8h;Heating / reflux; | Example 9 N-Hydroxy-2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionamide. To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 gm, 20 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring.. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated.. The residue was extracted with chloroform and washed with H2O and 0.5 N NaOH solution.. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield: 4.4 g (100%); MS; 227 (M+H)+. |
100% | With potassium carbonate; In acetone; for 8h;Heating / reflux; | Example 831-Benzyl-4-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylic Acid hydroxyamide To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 gm, 20 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O and 0.5 N NaOH solution. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield: 4.4 g (100%); MS; 227 (M+H)+. |
100% | With potassium carbonate; In acetone; for 8h;Heating / reflux; | To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 gm, 20 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extacted with chloroform and washed with H2O and 0.5 N NaOH solution. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield 4.4 g (100%); MS; 227 (M+H)+. |
98% | With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 1h; | Part A. (4-Methoxy-phenylsulfanyl)-acetic acid ethyl ester To a suspension of sodium hydride (60% in oil, 1.71 g, 42.8 mmol) in THF (40 mL), 4-methoxybenzenethiol (5.0 g, 35.7 mmol) was added dropwise at room temperature over a period of 10 min. The mixture was stirred at room temperature under N2 for 10 min and then cooled to 0 C. Ethyl bromoacetate (4.0 mL, 36 mmol) was added dropwise at 0 C. over a period of 10 min. The reaction mixture was stirred at room temperature for 30 min and then quenched with saturated ammonium chloride. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2*). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (1:9 ethyl acetate/hexanes) to provide (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester (7.9 g, 98%) as colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.42 (d, J=6.6 Hz, 2H), 6.84 (d, J=6.6 Hz, 2H), 4.11 (q, J=7.1 Hz, 2H), 3.80 (s, 3H), 3.51 (s, 2H), 1.21 (t, J=7.1 Hz, 3H); ESI MS m/z 227 [(M+H)+, calcd for C11H15O3S, 227.0]. |
92% | With triethylamine; In tetrahydrofuran; at 20℃; | Reference Example 39 ethyl [(4-methoxyphenyl)thio]acetate To an ice-cooled mixture of 4-methoxythiophenol (15 g, 0.11 mol), triethylamine (28 mL, 0.20 mol) and tetrahydrofuran (150 mL) was added ethyl bromoacetate (21 g, 0.13 mol), and the mixture was stirred overnight at room temperature. Ethanol (10 mL) was added, the solvent was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10:1) to give title compound (22 g, yield 92%). oil. 1H NMR (CDCl3) δ 1.22 (3H, t, J=7.1 Hz), 3.51 (2H, s), 3.79 (3H, s), 4.14 (2H, q, J=7.1 Hz), 6.83 (2H, d, J=8.8 Hz), 7.42 (2H, d, J=8.8 Hz). |
With potassium carbonate; In acetonitrile; at 0 - 20℃; for 3h; | 1st step: the 4 - methoxybenzenethiol (0.88 ml, 7 . 13mmol) dissolved in 15 ml acetonitrile in, adding potassium carbonate (2.96g, 21 . 4mmol), the obtained mixed liquid in cooling in ice, instillment bromine ethyl acetate (1.03 ml, 9 . 27mmol) acetonitrile solution (5 ml), during the dropping control in warm lower than 0 C, then completing, the resulting brown reaction solution is room temperature stirring 3h, TLC detection after the reaction is complete, water 30 ml dilution, ethyl acetate (30 ml × 4) extraction, the combined organic phase sequentially 1N NaOH (20 ml × 1), 1N HCl (20 ml × 1), saturated NaCl solution (20 ml × 2) washing, to obtained organic phase dried with anhydrous sodium sulfate, filtered, filtrate is decompressed and evaporate solvent to obtain amber oily liquid 1.8g, crude yield 112%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; | Ethyl (4-methoxyphenylthio)acetate may be prepared in the following manner: The procedure is as in Example 2 for the preparation of ethyl (phenylthio)acetate starting with ethyl bromoacetate (11.7 g), a 2M ethanolic solution of sodium ethylate (35 cc) and 4-methoxythiophenol (10 g). Ethyl (4-methoxyphenylthio)acetate (13.6 g) is thereby obtained, and is used in the crude state in the subsequent syntheses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.4 g (100%) | With potassium carbonate; In acetone; | EXAMPLE 9 N-Hydroxy-2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionamide. To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 gm, 20 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O and 0.5 N NaOH solution. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield: 4.4 g (100%); MS; 227 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; for 18h;Inert atmosphere; Reflux; | 4,7-dibromo- lH-benzo[d]imidazole ( lc) (150 mg, 0.54 mmol) was dissolved in dry 1 ,4-dioxane (5 ml) under stirring to which diisopropylethyl amine (281 mg, 1.63 mmol) was added. The reaction mixture was evacuated and backfilled with nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (24.88 mg, 0.027 mmol), xantphos (31.41 mg, 0.054 mmol) and 4-methoxybenzenethiol (0.2 ml, 1.63 mmol) were added and the reaction mixture was again degassed twice more. The reaction mixture was heated to reflux for 18 hour. After the completion of reaction, the reaction mixture allowed to reach ambient temperature, filtered and concentrated. The crude product so obtained was purified by flash column chromatography to afford 4,7-bis((4-methox rphenyl)thio)- lH-benzo[d]imidazole ( Id) (50 mg, 23% ) as an oil. MS (EI) m/z: 395. 1 (M+l ). iH NMR (400 MHz, DMSO-d6): 8 12.85 (s, 1H), 8.24 (s, 1H), 7.49 (d, J = 8.8 Hz, 2H), 7.24 (d, J = 8.8 Hz, 2H), 7.03-7.09 (m, 4H), 6.89 (d, J = 8.8 Hz, 1H), 6.46 (d, J = 8.8 Hz, 1H), 3.79 (s, 3H), 3.70 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.3% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; | N*3*-[3,5-Dichloro-4-(4-methoxy-phenylsulfanyl)-phenyl]-lH-[l,2,4]triazole-3,5-diamine mpound 16) (2,6-dichloro-4-nitrophenyl)(4-methoxyphenyl)sulfane In a 250-mL round-bottomed flask, 4-methoxybenzenethiol (1.00 g, 633 mu, 7.14 mmol, Eq: 1.00), l,3-dichloro-2-fluoro-5-nitrobenzene (1.5 g, 7.14 mmol, Eq: 1.00) and potassium carbonate (990 mg, 7.16 mmol, Eq: 1.00) were combined with N,N-dimethylformamide (20 mL) to give a yellow suspension. The reaction mixture was stirred overnight at room temperature. In the morning TLC was consistent with the reaction having reached completion. The reaction mixture was poured into water to give a yellow cloudy suspension. This suspension was extracted with ethyl acetate. The organic phase was dried over Sodium sulfate, filtered, then concentrated to give a brown oil which was loaded directly onto a 120 gram silica gel column. Flash chromatography 5 - 15% EtOAC in hexanes was used to purify the product, however, this purification was not very successful. The fractions containing the product were concentrated. 1H NMR showed that the product was consistent with product with only a small impurity. Obtained 2.2 g (93.3%) of (2,6-dichloro-4-nitrophenyl)(4-methoxyphenyl)sulfane as a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With silver trifluoromethanesulfonate; In dichloromethane; at 20℃; for 0.166667h; | General procedure: To a stirred solution of 2-alkynylbenzaldehyde 1 (0.5mmol, 1 equiv) and silver triflate (0.05 mmol, 13 mg, 0.01equiv) in dichloromethane (2.0 mL), was added thiol 2 (1.1mmol, 2.2 equiv). The mixture was stirred at ambient temperature for the appropriate time (see Table 2). After completionof the reaction as indicated by TLC, the solvent wasevaporated and the residue was purified by column chromatographyon silica gel to provide the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
388 mg | 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. 2,4-Diamino-8-(dimethylamino)-5-((4-methoxyphenyl)thio)-5H-chromeno[2,3-b]pyridine-3-carbonitrile (1g): Compound 1g was prepared following the general procedure for the preparation of Compounds 1g-1i. An amount of 388 mg (0.90 mmol, 92%) 1g was obtained as a light pinkish solid. 1H-NMR (DMSO-d6, 400 MHz): delta 6.97 (d, 1H, J = 8.87 Hz), 6.79 (bs, 2H), 6.68 (m, 4H), 6.51 (m, 1H), 6.40 (m, 2H), 6.07 (m, 1H), 5.53 (s, 1H), 3.69 (s, 3H), 2.87 (s, 6H). 13C-NMR (DMSO-d6, 100 MHz): delta 160.0, 159.8, 159.4, 156.2, 151.8, 150.4, 137.6, 129.0, 121.8, 116.7, 113.7, 109.1, 108.5, 98.2, 87.1, 70.1, 55.1, 43.0, 40.0. MP = 172.9 C. Anal. calcd. for C22H21N5O2S C, 62.99; H, 5.05; N, 16.69. Found C, 63.01; H, 5.08; N, 16.64. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With caesium carbonate; In dimethyl sulfoxide; at 25℃; for 20h;Inert atmosphere; UV-irradiation; | A 25 mL storage flask was charged with a stir bar, flame dried under vacuum and back filled with nitrogen three times. The flask was then charged with Cs2CO3 (97.7 mg, 0.3 mmol, 1.5 eq.), 1-iodo-2-methylbenzene (43.6 mg, 0.2 mmol, 1.00 eq.), 4-methoxybenzenethiol (42.0 mg, 0.3 mmol, 1.5 eq.) and 1.5 mL DMSO. The reaction mixture was evacuated and purged with inert gas (N2) three times. The reaction mixture was then placed into an LED-lined beaker and stirred with an air gas tube for cooling. After stirred for 20 hours, the reaction mixture was washed with water, extracted with EtOA and concentrated in vacuum. The product was isolated by flash chromatography (1:40 EtOAc:hexanes) as colorless oil (X=I, 25 mg, 54%). Physical State: colorless oil; Rf=0.4 (silica gel, hexanes); 1H NMR (300 MHz, CDCl3) δ 7.36-7.31 (m, 2H), 7.19-7.17 (m, 1H), 7.13-7.03 (m, 2H), 6.99 (dd, J=6.6, 1.8 Hz, 1H), 6.91-6.87 (m, 2H), 3.82 (s, 3H), 2.39 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 159.5, 137.1, 134.5, 130.2, 129.1, 126.5, 126.1, 124.5, 115.0, 55.4, 20.3; HRMS (ESI-TOF): m/z calcd. for C14H14OS ([M]+) 230.0765, found 230.0772. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | In 1-methyl-pyrrolidin-2-one; at 20℃; for 36h; | In a quartz tube, add 7 mmol of 7-methoxyquinoxaline-2- (1H) ketone (0.0880 g), 1 mmol of 4-methoxythiophenol (0.14 g), and N-methyl solvent 1.5 ml of pyrrolidone, reacted at room temperature under 9 watts of blue light for 36 hours at room temperature. The reaction was followed by thin layer chromatography. After the reaction was completed, the reaction was poured into 10-30 ml of water and extracted with 20-30 ml of ethyl acetate. 10-20 ml was washed three times, and finally dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure, and purified by flash silica gel column chromatography (ethyl acetate / petroleum ether = 1: 5-10) to obtain 3j as a white solid, yield 46%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In 1-methyl-pyrrolidin-2-one; at 20℃; for 36h; | In a quartz tube, 6-bromoquinoxaline-2- (1H) one 0.5 mmol (0.1120 g), 4-methoxythiophenol 1 mmol (0.14 g), and N-methylpyrrolidone 1.5 were added in this order. Ml, reacted at room temperature for 36 hours under 9 watts of blue light, followed by thin layer chromatography to track the reaction. After the reaction was completed, the reaction was poured into 10-30 ml of water, extracted with 20-30 ml of ethyl acetate, and saturated saline 10- 20 ml was washed three times, and finally dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure, and purified by flash silica gel column chromatography (ethyl acetate / petroleum ether = 1: 5-10) to obtain 3q as a yellow solid with a yield of 63% . |
A134464 [1774-36-3]
4,4'-Sulfinylbis(methoxybenzene)
Similarity: 0.67
A134464 [1774-36-3]
4,4'-Sulfinylbis(methoxybenzene)
Similarity: 0.67