Structure of 112-51-6
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| CAS No. : | 112-51-6 |
| Formula : | C10H22S2 |
| M.W : | 206.41 |
| SMILES Code : | CCCCCSSCCCCC |
| English Name : | Di-n-amyldisulfide |
| MDL No. : | MFCD00039964 |
| InChI Key : | YSQZSPCQDXHJDJ-UHFFFAOYSA-N |
| Pubchem ID : | 8191 |
* 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 |
|---|---|---|
| 88% | With sulfur; PEG-400; sodium hydroxide In N,N-dimethyl-formamide for 0.1h; microwave irradiation; | |
| 87% | With Amberlyst A-26 (disulphide form) In benzene for 9h; Heating; | |
| 76% | With PEG-400; sodium hydroxide; sulfur In benzene at 65℃; for 1h; |
| With sodium disulfide; water at 50℃; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 54% | With 3H-2,1-benzoxaselenole Se-oxide; dihydrogen peroxide In methanol; dichloromethane at 20℃; for 3h; | 3.2. Typical Procedure: Preparation S-Benzyl Phenylmethanesulfinothioate (2a) General procedure: Dibenzyl disulfide (245 mg, 1.00 mmol) and cyclic seleninate ester 1 (20 mg, 0.10 mmol) weredissolved in 10 mL of dichloromethane at room temperature with stirring. Hydrogen peroxide (127 μL,26.4% w/v, 1.00 mmol) was added to the solution. The mixture was stirred at room temperature andprogress was monitored by TLC. After 3 h, the reaction was diluted with dichloromethane, washed withbrine and dried with Na2SO4. The product was purified by flash chromatography on silica gel (hexane-ethylacetate, 10:1) to afford 139 mg (53%) of 2a. The product had properties identical to those reportedpreviously [18]. When the reaction was repeated in dichloromethane-methanol (95:5), a slightly higher yieldof 64% was obtained. The other thiolsulfinates in Tables 2 and 3 were prepared similarly, with any changesto the above conditions as noted in the Tables. Characterization data for the other products follows. |
| With dihydrogen peroxide; acetic acid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 99% | With water; dihydrogen peroxide In various solvent(s) at 20℃; for 0.166667h; | |
| 98% | With aluminum oxide In neat (no solvent) for 0.333333h; Milling; chemoselective reaction; | |
| 97% | With oxygen In dichloromethane at 0℃; for 0.166667h; |
| 96% | With chloro(4-1,5-cyclooctadiene)(1,3-bis(2,4,6-tris(diphenylmethyl)phenylimidazol-2-ylidene))rhodium(I) In neat (no solvent) at 20℃; | |
| 94% | With dihydrogen peroxide; tetra-(n-butyl)ammonium iodide In water at 20℃; for 0.166667h; Large scale reaction; | |
| 93% | With diethylamine In water at 20℃; for 4h; | |
| 92% | With potassium permanganate In dichloromethane at 20℃; for 0.916667h; | |
| 92% | With oxygen; dinitrogen tetraoxide; pyrographite In chloroform at 20℃; for 1.33333h; | |
| 92% | With 4,4′-azopyridine In acetonitrile at 80℃; for 2h; | Sample procedure for the synthesis of benzyl disulfide from benzyl mercaptan by oxidation with 4,4’-azopyridine General procedure: In a round-bottomed flask, a solution of benzyl mercaptan (2 mmol, 0.234 mL) in refluxing CH3CN (4 mL) was treated with 4,4’-azopyridine (1.1 mmol, 0.202 g). The resultingred solution was stirred at 80°C for 2 h. After decolorization of the red solution (indication ofcompletion of the reaction) and disappearance of benzyl mercaptan on TLC, the reaction mixturewas filtered to remove the hydrazine by-product. The filtrate was washed twice with 10% NaOHsolution (8 mL), then with saturated brine and was dried over anhydrous Na2SO4. Removal ofthe volatile compounds and solvent afforded a viscous oil. The product was purified by shortcolumnchromatography on silica gel eluted with n-hexane. Dipentyl disulfide (4c) colorless oil; 1H NMR (250 MHz, CDCl3): δ 0.93 (t, J = 7.2 Hz,6H), 1.36-1.41 (m, 8H), 1.61-1.1.68 (m, 4H), 2.66 (t, J = 7.4 Hz, 4H); 13C NMR (62.5 MHz,CDCl3): δ 39.4, 29.5, 29.0, 22.1, 14.2. Anal. Calcd. C10H22S2: C, 58.19%; H, 10.74%; S, 31.06%.Found: C, 58.10%; H, 10.67%; S, 31.23%. |
| 91% | With potassium permanganate supported on montmorillonite K10 at 20℃; for 0.416667h; | |
| 90% | With ethylenebis(N-methylimidazolium) chlorochromate In acetonitrile at 20℃; for 0.0833333h; | |
| 90% | With sodium hydrogensulfite; periodic acid In water at 20℃; for 0.416667h; | |
| 90% | With silica gel-supported iodine monochloride In chloroform at 20℃; for 0.75h; | |
| 89% | With potassium phosphate; air In acetonitrile at 37℃; for 12h; | |
| 89% | With pyridinium hydrobromide perbromide at 20℃; for 0.133333h; Neat (no solvent); | |
| 87% | With Tetramethylammonium Chlorochromate In acetonitrile for 2h; Heating; | |
| 87% | With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 1.1h; Heating; | |
| 87% | With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In acetonitrile for 1.1h; Heating; | |
| 86% | With Fe-EDTA; oxygen In methanol; water at 30℃; for 9h; pH = 9.5; | |
| 86% | With potassium permanganate; copper(II) sulfate In dichloromethane for 2h; Ambient temperature; | |
| 86% | With sodium hydroxide; cobalt phthalocyaninetetrasulphonamide; oxygen In water at 20℃; for 0.416667h; | |
| 86% | With tetrabutylammonium peroxydisulfate at 20℃; for 0.0833333h; | |
| 86% | With TriPAFC/Al2O3 In dichloromethane for 1.53333h; | |
| 85% | With silica gel; pyridinium fluorochromate In acetonitrile for 0.116667h; Microwave irradiation; | |
| 85% | With potassium bromate; hexaammonium heptamolybdate tetrahydrate In water; acetonitrile at 20℃; for 0.333333h; | Typical Procedure General procedure: 4-chlorothiophenol (0.145 g, 1 mmol) was added to a heterogeneous mixture of KBrO3 (0.167 g, 1 mmol), (NH4)6Mo7O24·4H2O (0.124 g, 10 mmol%), and CH3CN/H2O (7:3) (5 mL) and the mixture was stirred under a hood for 4 min at ambient atmosphere and room temperature. The progress of the reaction was monitored by TLC (eluent: EtOAc/n-C6H14, 1/13). After completion, CH2Cl2 (20 mL) was added and the reaction mixture was filtered. The filtrate was washed with 5% NaOH, water, and dried over anhydrous MgSO4. Finally, evaporation of the solvent gave the product with sufficient purity formost purposes |
| 84% | With dipotassium peroxodisulfate; 1-n-butyl-3-methylimidazolim bromide at 65 - 70℃; for 0.5h; | |
| 83% | With potassium iodate; dimethyl sulfoxide In acetonitrile at 20℃; for 5h; | 3; 10 Example 3: Catalytic oxidation of n-pentanethiol to prepare dipentyl disulfide - batch reaction process (using KIO3)4(Taking catalysts as an example) In a clean, dry 250 mL round-bottom flask, under air atmosphere, the metal catalyst KIO3 was added sequentially.4(55.2 mg, 0.24 mmol), acetonitrile (100 mL) as organic solvent, n-pentanethiol (50.0 g, 480.0 mmol) as reactant, and dimethyl sulfoxide (18.8 mg, 0.24 mmol) as oxidant were used. The mixture was stirred at room temperature for 5 hours. The organic phase was extracted with petroleum ether and water. The organic phase was then distilled to remove the organic solvent, yielding dipentyl disulfide with a separation yield of 83.0% and a sample purity of 98.4%. |
| 81% | With oxygen; cesium fluoride In acetonitrile at 20℃; | |
| 81% | With periodic acid; sodium hydrogensulfite In tetrachloromethane; water at 20℃; | |
| 81% | With hexamethylene bis(N-methylimidazolium)bis(dichloroiodate) In neat (no solvent) at 20℃; for 0.166667h; | General procedure for the oxidative coupling of thiols into disulfides with HMBMIBDCI General procedure: Thiophenol (0.5 mmol, 55 mg) was treated with HMBMIBDCI (0.25 mmol, 161 mg) in solvent-free conditions at room temperature for the specified time shown in Table 3. After disappearance of the starting material as monitored by GC, the reaction was quenched with water (20 ml) and was extracted with Et2O (40 ml). The organic layer was washed with aqueous NaHSO3 (5%, 20 ml), dried over MgSO4, and evaporated under reduced pressure. The crude material obtained was practically pure in most cases with no need for further purification. Otherwise, the crude products were purified by recrystallization or preparative TLC. All the products were identified by comparing melting point and 1H and 13C NMR with those of authentic samples reported in the literature. Dipentyldisulfide (Table 3, entry 11). Oil [44]; 1H NMR (400 MHz, CDCl3): δ (ppm) = 2.70 (t, J = 7.4, 2 H), 1.70 (quin, J = 7.4 Hz, 2 H), 1.40-1.34 (m, 4 H), 0.93 (t, J = 7.2 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ (ppm) = 39.18, 30.71, 28.93, 22.33, 13.99. |
| 79% | With 18-crown-6 ether; carbon tetrabromide; potassium carbonate In benzene at 20℃; for 6h; | |
| 74% | With tributylammonium fluorochromate absorbed on silica gel In dichloromethane at 20℃; for 1.08333h; | |
| With sodium hydroxide; iodine | ||
| With lead(IV) acetate; benzene | ||
| With pyridine; ethanol; iodine | ||
| With dimethylsulfide; dinitrogen monoxide In water Irradiation; γ-irradiation; | ||
| With bromine Ambient temperature; Yield given; | ||
| Multi-step reaction with 2 steps 1: 80 percent / bis-benzotriazole selenide / CH2Cl2 / 3 h 2: triphenylphosphine | ||
| Multi-step reaction with 2 steps 1: bis-benzotriazole selenide / CH2Cl2 / 3 h 2: triphenylphosphine | ||
| With 1-octly-3-methylimidazolium persulfate at 80℃; for 1h; neat (no solvent); | ||
| With oxygen; benzylamine; copper dichloride In 2,2,4-trimethylpentane at 25℃; | ||
| 85 %Spectr. | With graphene oxide In tetrahydrofuran at 60℃; | |
| 76 %Chromat. | With [RuCl(PPh3)2(3-phenylindenyl)]; potassium hydroxide In methanol at 60℃; for 1.5h; Glovebox; | |
| 88 %Chromat. | With silica supported on iron oxide at 20℃; for 5h; Green chemistry; | |
| With C222H156Fe4N24(8+)*8C2F6NO4S2(1-) In [D3]acetonitrile at 50℃; for 11.5h; Sealed tube; | ||
| With dihydrogen peroxide; iodine | ||
| 99 % | With tris(4-aminophenyl)amine and (2,2’-bipyridine)-5,5’-dicarbaldehyde-based covalent organic framework In acetonitrile at 18℃; Irradiation; | |
| With potassium carbonate In acetonitrile at 20℃; | ||
| With bromine at 20℃; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 96% | With sulfuryl dichloride; acetic anhydride In dichloromethane at -10℃; for 1.5h; | |
| 96% | With thionyl chloride; acetic anhydride In dichloromethane at -10℃; for 1.5h; | 3.1 (1) Preparation of Pentylsulfinyl Chloride To a reaction flask were added dipentyl disulfide (33 mmol), acetic anhydride (6.8 g, 66 mmol), and dichloromethane (100 mL). The reaction mixture was cooled to -10 °C, and then thionyl chloride (14.9 g, 109 mmol) was added dropwise, maintaining the temperature of the reaction mixture below 5 °C during the addition. After the addition was complete, the reaction mixture was stirred at -10 °C for 1.5 h. After the reaction, the resulting product mixture was distilled under reduced pressure at room temperature to remove acetyl chloride and dichloromethane, yielding the crude product. The crude product was then distilled under reduced pressure to obtain a pale yellow oily substance, which was pentylsulfinyl chloride (boiling point: 60 °C/0.405 mmHg), with a yield of 9.76 g and a yield rate of 96%. |
| 77% | With pyridine; acetic anhydride; chlorine In diethyl ether; water at -20 - -10℃; |
| With chlorine; acetic acid at -15 - -10℃; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With H4Mo2S12(2-)*2H(1+)*2H3N In benzene at 90℃; acetonitrile; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | ||
| 1: 59 %Chromat. 2: 16 %Chromat. | With sulfide ion In tetrahydrofuran; water at 20℃; for 12h; Inert atmosphere; Green chemistry; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 97% | With hydrogenchloride | 6.6 Example 6-6 Example 6-6 2-(3-Bromo-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (400 mg, 1.41 mmol) obtained in the same manner as in Example 6-1 and THF (4 ml) were mixed, and this solution was cooled to -60° C. n-Butyllithium (1.6M hexane solution, 1.94 ml, 3.1 mmol) was added and the mixture was stirred for 1.5 hours. Di-n-amyldisulfide (0.69 ml, 3.1 mmol) was added to this reaction mixture, and the mixture was stirred for 4 hours at room temperature. To the mixture was added 1N hydrochloric acid (2 ml), and the aqueous layer was extracted 3 times with ethyl acetate (5 ml). The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=4/1) to give 2-(4-methoxy-3-pentylthiophenyl)-4,4-dimethyl-4,5-dihydrooxazole (422 mg, 97%) as a colorless oil. The properties of the compounds obtained in the above Example 6-1 to 6--6 are shown in Tables 106 and 107. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 84% | Stage #1: pentan-1-ol With 5,5'-dimethyl-3,3′-azoisooxazole; triphenylphosphine In acetonitrile at 80℃; for 0.333333h; Stage #2: With ammonium thiocyanate In acetonitrile at 80℃; for 4h; | General procedure for the conversion of aliphatic alcohols into the corresponding disulfides General procedure: The aliphatic alcohol (1 mmol) was added to a solution of azo compound 1a or 1e (1.8 mmol) and PPh3 (1.8 mmol) in refluxing CH3CN (5 mL) and the mixture was stirred for 20 min at 80 °C. Next, NH4SCN (2.5 mmol) was added in one portion. The resulting mixture was stirred at 80 °C for the appropriate time (Table 2), until consumption of the starting material was complete, as monitored by TLC and GC analyses. The mixture was filtered and the solvent evaporated. H2O (10 mL) was added and the product was extracted with Et2O (3 × 10 mL). The organic solution was dried (MgSO4) and evaporated. The obtained residue was purified by flash column chromatography on silica gel using petroleum ether as the eluent to give the disulfide. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen at 300℃; for 3h; Flow reactor; | 2.2. Catalytic measurements General procedure: The general procedure for the catalytic reaction is described for the benzene thiol/acetic acid/1 system. A conventional ver-tical glass fixed-bed microreactor with a continuous gas-flow system was operated at atmospheric pressure [10]. In each experiment, a weighed supported sample of 1/SiO2(30.0 mg) waspacked in a borosilicate glass tube (3 mm i.d.) with the aid of quartz glass and placed in the center of an electric furnace.The supported cluster sample was initially heated from room temperature to a fixed temperature between 50 and 500° C in15 min in a hydrogen stream (300 mL/h), and then it was heldat that temperature for 45 min for activation. Then, the reactionwas initiated by feeding a mixture of benzenethiol (102 L/h,1.0 mmol/h) and acetic acid (114 L/h, 2.0 mmol/h) into the hydrogen stream without changing the temperature. The reaction was monitored every 30 min by sampling the reaction gas (1 mL) with a Conversion, six-way valve kept at 150C followed by analysis using an online gas-liquid chromatograph (GLC) with a methyl silicone column. The reactor effluent was collected in an ice trap containing tetrahydrofuran for subsequent analyses by GLC with a poly(ethyleneglycol) capillary column or a dimethylpolysiloxane capillary col-umn and gas chromatography-mass spectrometry (GC-MS) witha dimethylpolysiloxane capillary column. Catalytic reactions usingthe other thiols, alkylating reagents, and catalysts were performedin the same way. In this paper, conversion and selectivity aredefined as follows: conversion = products/(products + recoveredthiol) × 100 (%), and selectivity = product/(total amount of prod-ucts) × 100 (%) based on thiol. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1: 61% 2: 10% | With graphene oxide In neat (no solvent) at 60℃; for 3h; Green chemistry; chemoselective reaction; | General Procedure for the preparation of dithioacetal General procedure: To a mixture of aldehyde (1 mmol) and thiol (2.2 mmol), 50 mg of graphene oxide was addedand stirred the reaction mixture at room temperature for hours as mentioned in the Tables (2-4). After completion of reaction, diethyl ether (5 mL) was added, stirred gently and then allowed to stand. The supernatant liquid was carefully collected in another flask and this process was repeated three times more. The liquid part was concentrated and the residue waspurified through column chromatography over silica gel. Elution with light petroleum orethyl acetate-light petroleum (2:98) affords the pure dithioacetal (% Yield as mentioned in the Tables). All products were characterized by 1H, 13C NMR data and compared with thereported melting points for known solid compounds. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | With iodine In tetrahydrofuran at 50℃; for 9h; | 8 Preparation Example 8 In a 10 mL reaction tube was added disulfide II (R = n-butyl),Amines III (R1 = p-chlorophenyl, R2 = H) (1 eq) and elemental iodine (0.6 eq) were added and 1 mL of tetrahydrofuran was added dropwise. The reaction was carried out at 50 ° C for 9 h. After the reaction was completed, the title compound was isolated by column chromatography to give a yellow solid in a yield of 64%. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 100℃; for 12h; Schlenk technique; | 7 Example 7 In this example, 2-(pentylthio)benzonitrile (1g) was prepared. The reaction formula is as follows: Under an atmospheric air atmosphere,Into a 15mL Schlenk reaction tube, sequentially add imidate compound 2f (30.0mg, 0.20mmol), disulfide 3c (41.2mg, 0.20mmol), trivalent rhodium catalyst [Cp*RhCl2] 2 (1.2mg), silver salt of bistrifluoromethanesulfonimide (2.3mg), sodium acetate (4.6mg), copper acetate (20.0mg), 1,2-dichloroethane (DCE, 1mL), reacted at a temperature of 100 12 hours. After it should be finished, it was cooled to room temperature, filtered through celite, and concentrated to obtain a crude product. The crude product was chromatographed on a prepared silica gel plate. The selected developing agent or eluent was a volume ratio of petroleum ether and ethyl acetate of 50:1. The product 2-(pentylthio)benzonitrile (1 g) was isolated, 33.6 mg, and the yield was 82%. |
| 76% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; silver(I) triflimide In 1,2-dichloro-ethane at 100℃; for 12h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With ammonium iodide In acetonitrile at 20℃; for 2h; Electrochemical reaction; | General procedure for the synthesis of compounds 3a-3s. General procedure: In an oven-dried undivided three-necked bottle (25 mL) equipped with a stir bar, 3-(dimethylamino)-1-(2-hydroxyphenyl)-2-propen-1-one 1a (0.2 mmol), disulfide 4a (0.14 mmol), ammonium iodide (30 mol%), CH3CN (5 mL) was added. The bottle was equipped with platinum plate (10 mm×10 mm×1 mm) as the anode and platinum plate (10 mm×10 mm×1 mm) as the cathode. The reaction mixture was stirred and electrolyzed at a constant current of 10 mA under air at room temperature for 2 h. After completion of the reaction, as indicated by TLC and GC-MS, the pure product was obtained by flash column chromatography on silica gel (petroleum ether : ethyl acetate = 15 : 1). The same procedure was applied to the production of other compounds 3a-3s. |