CN108484456A - A kind of method of selectively oxidizing sulfur ether - Google Patents

A kind of method of selectively oxidizing sulfur ether Download PDF

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Publication number
CN108484456A
CN108484456A CN201810101831.6A CN201810101831A CN108484456A CN 108484456 A CN108484456 A CN 108484456A CN 201810101831 A CN201810101831 A CN 201810101831A CN 108484456 A CN108484456 A CN 108484456A
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formula
reaction
phenyl
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thioether
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谢媛媛
蒋筱莹
童踔
张长俊
米治胜
甘兵
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Zhejiang University of Technology ZJUT
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a kind of method of selectively oxidizing sulfur ether, a kind of new synthetic method of sulfoxide compound shown in formula (I) is disclosed：Using thioether is raw material shown in formula (II), in the presence of tert-butyl hydroperoxide, oxidation reaction occurs in a solvent, it is after reaction, post-treated to obtain sulfoxide compound shown in formula (I).Compared with the conventional method, present invention employs green friendly oxidant tert-butyl hydroperoxide, the use of metallic catalyst is avoided, reaction condition is mild, high selectivity, easy to operate, and substrate applicability is wide, and reaction yield is high.

Description

A kind of method of selectively oxidizing sulfur ether
Technical field
The present invention relates to the new methods that a kind of selectively oxidizing sulfur ether generates sulfoxide compound, belong to organic synthesis neck Domain.
Background technology
Sulfoxide compound has extensive biological activity, the structure is all had in many drugs, for example contain sulfoxide The most typical medicine of structure is anti-ulcer agent Omeprazole, in addition, such compound is in anti-arrhythmia, heart failure resistance, anti- It is obtained for and is widely applied in tumour medicine and agrochemical medicine and pesticide field.In recent years, to sulfoxide compound into The sulfoxide compound with more high bioactivity is found in row structure optimization, influence of the research structure to bioactivity, it has also become One of the hot spot that pharmaceutical chemistry circle scholars study.
Sulfoxide compound is also a kind of very important intermediate in organic synthesis, can be by participating in different reactions Synthesize various active materials.It can synthesize the sulphoxide imine class compound with more preferable bioactivity by imidization； Sulfone compound can be obtained by catalytic oxidation；It can be used as raceme and obtain chiral sulfoxide under the action of chiral resolving agent Class compound.Therefore, synthesizing the various sulfoxide compounds for having potential use has very important value.
The synthesis of sulfoxide compound is mainly obtained by the oxidation of thioether, and the selective oxidation of thioether is at sulfoxide or sulfone It is the key that oxidation reaction and difficult point place.Numerous document reports synthesis of such compound, as Palmieri et al. is used Concentrated nitric acid and tetrabutyl chlorauride ammonium salt are aoxidized (Synthetic communications, 1984,14,1111-1117)； Asady et al. is aoxidized (Synthetic communications, 2005,35,775- using acid iodide and silica 784)；Beller et al. is aoxidized (Adv.Synth.Catal., 2007,349,2425-2430) using hydrogen peroxide, but this A little methods use poisonous and harmful expensive reagent, or the not high substrate applicability of selectivity is not wide, or are easy the bottom of Object peroxidating generates sulfone.Therefore, develop that a kind of raw material is easy to get, the method for high-efficient simple carrys out selectively oxidizing sulfur ether to sulfoxide very It is necessary.The present invention using cheap green oxidant tert-butyl hydroperoxide, it is highly selective by sulfide oxidation at sulfoxide, no mistake Oxidized byproduct generates, easy to operate, product yield high.
Invention content
The purpose of the present invention is to provide a kind of new method of selectively oxidizing sulfur ether, the synthesis of green close friend's simple and effective Sulfoxide compound.
To achieve the above object, the present invention adopts the following technical scheme that：
A kind of method that selectively oxidizing sulfur ether prepares sulfoxide compound shown in formula (I), the method are：By formula (II) thioether shown in is dissolved in solvent, and tert-butyl hydroperoxide is added as oxidant, 1- is reacted at a temperature of 30-100 DEG C For 24 hours, after reaction (TLC detections), reaction solution is post-treated obtains sulfoxide compound shown in formula (I)；The formula (II) Shown in the amount ratio of substance of thioether and the tert-butyl hydroperoxide be 1:2~10；
In formula (II) or formula (I), R1、R2Respectively stand alone as Cl-C6 alkyl, alkynyl, alkenyl, alkoxy, benzyl, heterocycle, benzene Base or substituted-phenyl, the substituted-phenyl are that the substituted bases of H on phenyl are monosubstituted or polysubstituted, and the number of the substituent group is 1-3, the substituent group respectively stands alone as C1-C4 alkyl, alkoxy, hydroxyl, aldehyde radical, F, Cl or Br.
The synthetic route of the present invention is as follows：
Preferably, in the above method, in formula (II) or formula (I), R1、R2Respectively stand alone as phenyl, methyl, benzyl, to methoxy Base phenyl, to aldehyde radical phenyl, rubigan, phenylol, p-methylphenyl or p-bromophenyl.
Further, in the above method, thioether shown in the formula (II) and the substance of the tert-butyl hydroperoxide Amount is than preferably 1:4~6.
Further, in the above method, the solvent is 1,2- dichloroethanes, dichloromethane, chloroform, carbon tetrachloride, second One kind in nitrile, acetone, ethyl acetate, dioxane, tetrahydrofuran, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide Or a variety of, preferably 1,2- dichloroethanes, dichloromethane or chloroform.
Further, in the above method, the volumetric usage of the solvent is with the gauge of the substance of thioether shown in formula (II) For 2~6 mL/mmol, preferably 2mL/mmol.
Further, in the above method, the reaction temperature of the reaction is 30~100 DEG C, preferably 60-90 DEG C.
Further, in the above method, the reaction time of the reaction is 1-24h, preferably 1.5-10h.
Further, in the above method, the post-processing is：After reaction, be added water (dosage of the water recommend with The amount of the substance of thioether shown in formula (II) is calculated as 5mL/mmol), (3 × 5mL/mmol) is extracted with dichloromethane, is merged organic Layer is simultaneously dry, is concentrated under reduced pressure, with petroleum ether：Ethyl acetate is 20:1 mixed liquor is solvent, and formula (I) is obtained through column chromatography for separation Shown in sulfoxide compound.
Further, in the above method, sulfoxide compound shown in formula (I) is one of following compounds：
The structure warp of gained compound (I) of the invention1H NMR、13The methods of C NMR, MS, HRMS are characterized and are confirmed.
Beneficial effects of the present invention：It is in the prior art sulfoxide compound by sulfide oxidation, mainly uses following several Catalyst system and catalyzing：Tetrabutyl iodate auramine, silver nitrate metallic catalyst are such as used, but expensive；Using concentrated nitric acid, acid iodide etc. Catalyst, it is dangerous, generate pollutant；When making catalyst using hydrogen peroxide, solvent-free reaction substrate applicability is narrow, sulfoxide production Object yield is low, can be further oxidized to sulfone；And the technology of the present invention uses nonmetallic cheap reagent, can be incited somebody to action under suitable dosage Substrate selective is oxidized to sulfoxide, will not be further oxidized to sulfone, and yield can reach 90% or more substantially.Therefore present invention operation Simplicity, reaction condition is mild, and high selectivity, product yield high, substrate applicability is wide, meets the requirement of Green Chemistry.
Specific embodiment
With specific embodiment, the following further describes the technical solution of the present invention below, but protection scope of the present invention It is without being limited thereto.
Embodiment 1
Thioanisole (20mmol, 2.48g) is sequentially added in 100mL single port bottles, mass fraction is 70% tertiary butyl mistake Hydrogen oxide (100mmol, 12.86g) and 40mL chloroforms react 1.5h at 60 DEG C.(TLC monitorings) after reaction stops heating, After being cooled to room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, decompression is dense Contracting, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) yellow oily target product, yield 98% (2.74g) are obtained.
1H NMR(500MHz,CDCl3):δ7.67-7.62(m,2H),7.55-7.46(m,3H),2.72(s,3H)；13C NMR (100MHz,CDCl3)δ145.3,130.8,129.1,123.2,43.9；HRMS(ESI)calcd for C5H5N2OS[M+ H]+141.0116；found 141.0117.
Embodiment 2
4- methyl thiobenzoxides (20mmol, 2.76g), 70% tert-butyl hydroperoxide are sequentially added in 100mL single port bottles Hydrogen (120 mmol, 15.43g) and 40mL dichloromethane react 10h at 50 DEG C.(TLC monitorings) after reaction stops heating, After being cooled to room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, decompression is dense Contracting, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) yellow oily target product, yield 90% (2.77g) are obtained.
1H NMR(400MHz,CDCl3) δ 7.52 (d, J=8.2Hz, 2H), 7.31 (d, J=8.2Hz, 2H), 2.70 (s, 3H), 2.41(s,3H)；13C NMR(100MHz,CDCl3)δ142.0,141.1,129.7,123.2,43.9,21.4；MS (ESI)330.7 [2M+Na]+.
Embodiment 3
4- methoxybenzenes methyl sulfide (20mmol, 3.08g), 70% t-butyl peroxy are sequentially added in 100mL single port bottles Change hydrogen (100mmol, 12.86g) and 40mL1,2- dichloroethanes, reacts 3h at 85 DEG C.(TLC monitorings) after reaction stops Heating after being cooled to room temperature, is added 100mL water, then extract (3 × 100mL) with dichloromethane, merges organic layer and drying, subtract Pressure concentration, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) white object product, yield 95% (3.23g) are obtained.
Fusing point：40-42℃；1H NMR(400MHz,CDCl3) δ 7.58 (d, J=8.8Hz, 2H), 7.02 (d, J=8.8Hz, 2H),3.84(s,3H),2.69(s,3H)；13C NMR(125MHz,CDCl3)δ161.9,136.5,125.4,114.8,55.5, 43.9；MS(ESI)171.1[M+H]+.
Embodiment 4
4- bromophenyl sulfides (20mmol, 4.04g), 70% tert-butyl hydroperoxide are sequentially added in 100mL single port bottles (80 mmol, 10.29g) and 40mL acetonitriles react for 24 hours at 80 DEG C.(TLC monitorings) after reaction stops heating, is cooled to After room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, be concentrated under reduced pressure, column layer Analyse (solvent：Petroleum ether：Ethyl acetate=20:1) white object product, yield 81% (3.53g) are obtained.
Fusing point：76-81℃；1H NMR(400MHz,CDCl3) δ 7.68 (d, J=8.6Hz, 2H), 7.53 (d, J=8.6Hz, 2H),2.72(s,3H)；13C NMR(100MHz,CDCl3)δ144.9,132.5,125.4,125.1,44.0；MS(ESI)218.9 [M+H]+.
Embodiment 5
Benzaldehyde -4- methyl sulfides (20mmol, 3.04g), 70% tert-butyl hydroperoxide are sequentially added in 100mL single port bottles Hydrogen (100 mmol, 12.86g) and 40mL ethyl acetate react 12h at 75 DEG C.(TLC monitorings) after reaction stops heating, After being cooled to room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, decompression is dense Contracting, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) white object product, yield 90% (3.02g) are obtained.
Fusing point：83-84℃；1H NMR(500MHz,CDCl3) δ 10.07 (s, 1H), 8.03 (d, J=8.2Hz, 2H), 7.81 (d, J=8.2Hz, 2H), 2.77 (s, 3H)；13C NMR(125MHz,CDCl3)δ191.1,152.4,138.1,130.3, 124.1,43.7； MS(ESI)169.2[M+H]+.
Embodiment 6
4- methyl ethyl phenyl sulfide (20mmol, 3.04g), 70% tert-butyl hydroperoxide are sequentially added in 100mL single port bottles Hydrogen (140 mmol, 18.00g) and 40mL tetrahydrofurans react 8h at 65 DEG C.(TLC monitorings) after reaction stops heating, After being cooled to room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, decompression is dense Contracting, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) yellow oily target product, yield 68% (2.28g) are obtained.
1H NMR(500MHz,CDCl3) δ 7.49 (d, J=8.2Hz, 2H), 7.31 (d, J=8.2Hz, 2H), 2.87 (dq, J =13.4,7.4Hz, 1H), 2.81-2.72 (m, 1H), 2.40 (s, 3H), 1.17 (t, J=7.4Hz, 3H)；13C NMR (125MHz, CDCl3)δ141.4,139.8,129.8,124.2,50.2,21.3,6.0；MS(ESI)169.1[M+H]+.
Embodiment 7
P-methylphenyl allyl sulphide (20mmol, 3.28g), 70% tertiary butyl mistake are sequentially added in 100mL single port bottles Hydrogen oxide (60mmol, 7.71g) and 40mL chloroforms react 5h at 70 DEG C.(TLC monitorings) after reaction stops heating, cooling To room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, be concentrated under reduced pressure, column Chromatograph (solvent：Petroleum ether：Ethyl acetate=20:1) yellow oily target product, yield 52% (1.87g) are obtained.
1H NMR(500MHz,CDCl3) δ 7.49 (d, J=8.2Hz, 2H), 7.32 (d, J=8.2Hz, 2H), 5.64 (ddt, J=17.6,10.2,7.5Hz, 1H), 5.36-5.29 (m, 1H), 5.20 (dq, J=17.0,1.2Hz, 1H), 3.60-3.46 (m,2H), 2.41(s,3H)；13C NMR(125MHz,CDCl3)δ141.5,139.7,129.7,125.4,124.3,123.6, 60.9,21.4； MS(ESI)382.9[2M+Na]+.
Embodiment 8
P-methylphenyl propargyl thioether (20mmol, 3.24g), 70% tertiary butyl mistake are sequentially added in 100mL single port bottles Hydrogen oxide (160mmol, 20.57g) and 40mL carbon tetrachloride react 16h at 90 DEG C.(TLC monitorings) after reaction stops adding Heat after being cooled to room temperature, is added 100mL water, then extract (3 × 100mL) with dichloromethane, merges organic layer and drying, decompression Concentration, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) yellow oily target product, yield 60% (2.14g) are obtained.
1H NMR(500MHz,CDCl3) δ 7.60 (d, J=8.2Hz, 2H), 7.33 (d, J=8.2Hz, 2H), 3.68-3.62 (m, 1H), 3.62-3.56 (m, 1H), 2.42 (s, 3H), 2.34 (t, J=2.7Hz, 1H)；13C NMR(125MHz,CDCl3)δ 142.3,139.5,129.7,124.4,76.2,72.8,47.7,21.4；MS(ESI)178.9[M+H]+.
Embodiment 9
Rubigan benzyl thioether (20mmol, 4.68g), 70% t-butyl peroxy are sequentially added in 100mL single port bottles Change hydrogen (40mmol, 5.14g) and 40mL dichloromethane, reacts 20h at 30 DEG C.(TLC monitorings) after reaction stops heating, After being cooled to room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, decompression is dense Contracting, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) white object product, yield 40% (2.00g) are obtained.
Fusing point：130-131℃；1H NMR(400MHz,CDCl3)δ7.46-7.33(m,2H),7.34-7.16(m,5H), 6.95 (dd, J=7.7,1.3Hz, 2H), 4.09 (d, J=12.6Hz, 1H), 3.97 (d, J=12.6Hz, 1H)；13C NMR (125MHz, CDCl3)δ141.2,137.3,130.3,129.1,128.6,128.5,128.4,125.9,63.5；MS(ESI) 522.9[2M+Na]+.
Embodiment 10
Diphenyl sulfide (20mmol, 3.72g), 70% tert-butyl hydroperoxide are sequentially added in 100mL single port bottles (200mmol, 25.71g) and 40mL chloroforms react for 24 hours at 55 DEG C.(TLC monitorings) after reaction stops heating, is cooled to After room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, be concentrated under reduced pressure, column layer Analyse (solvent：Petroleum ether：Ethyl acetate=20:1) white object product, yield 15% (0.61g) are obtained.
Fusing point：69-70℃；1H NMR(500MHz,CDCl3)δ7.68-7.63(m,2H),7.50-7.43(m,3H)；13C NMR(125MHz,CDCl3)δ145.5,131.0,129.3,124.7；MS(ESI)203.1[M+H]+.
Embodiment 11
Para hydroxybenzene thioether (20mmol, 4.36g), 70% tert-butyl hydroperoxide are sequentially added in 100mL single port bottles (180 mmol, 23.14g) and 40mL n,N-Dimethylformamide react 4h at 100 DEG C.(TLC monitorings) after reaction, stops It only heats, after being cooled to room temperature, 100mL water is added, then (3 × 100mL) is extracted with dichloromethane, merges organic layer and drying, It is concentrated under reduced pressure, column chromatography (solvent：Petroleum ether：Ethyl acetate=20:1) white object product, yield 35% (1.64g) are obtained.
Fusing point：190-192℃；1H NMR(500MHz,CDCl3) δ 10.08 (s, 1H), 7.43 (d, J=8.6Hz, 2H), 6.87 (d, J=8.6Hz, 2H)；13C NMR(125MHz,CDCl3)δ159.9,135.5,126.5,116.1；MS(ESI) 235.0 [M+H]+。

Claims (8)

1. a kind of method that selectively oxidizing sulfur ether prepares sulfoxide compound shown in formula (I), it is characterised in that the method For：Thioether shown in formula (II) is dissolved in solvent, tert-butyl hydroperoxide is added as oxidant, at a temperature of 30-100 DEG C 1-24h is reacted, after reaction, reaction solution is post-treated to obtain sulfoxide compound shown in formula (I)；Shown in the formula (II) The amount ratio of substance of thioether and the tert-butyl hydroperoxide be 1:2~10；
In formula (II) or formula (I), R1、R2Respectively stand alone as Cl-C6 alkyl, alkynyl, alkenyl, alkoxy, benzyl, heterocycle, phenyl or Substituted-phenyl, the substituted-phenyl are that the substituted bases of H on phenyl are monosubstituted or polysubstituted, and the number of the substituent group is 1-3 A, the substituent group respectively stands alone as C1-C4 alkyl, alkoxy, hydroxyl, aldehyde radical, F, Cl or Br.
2. the method as described in claim 1, it is characterised in that：In formula (II) or formula (I), R1、R2Respectively stand alone as phenyl, first Base, benzyl, p-methoxyphenyl, to aldehyde radical phenyl, rubigan, phenylol, p-methylphenyl or p-bromophenyl.
3. the method as described in claim 1, it is characterised in that：The solvent is 1,2- dichloroethanes, dichloromethane, chlorine Imitative, carbon tetrachloride, acetonitrile, acetone, ethyl acetate, dioxane, tetrahydrofuran, N,N-dimethylformamide, N, N- dimethyl It is one or more in acetamide.
4. the method as described in claim 1, it is characterised in that：The volumetric usage of the solvent is with thioether shown in formula (II) The amount of substance be calculated as 2~6mL/mmol.
5. the method as described in claim 1, it is characterised in that：Thioether shown in the formula (II) and the t-butyl peroxy The amount ratio for changing the substance of hydrogen is 1:4~6.
6. the method as described in claim 1, it is characterised in that：The reaction temperature of the reaction is 60-90 DEG C.
7. the method as described in claim 1, it is characterised in that：The reaction time of the reaction is 1.5-10h.
8. the method as described in claim 1, it is characterised in that the post-processing is：After reaction, water is added, uses dichloromethane Alkane extracts, and merges organic layer and drying, is concentrated under reduced pressure, with petroleum ether：Ethyl acetate is 20:1 mixed liquor is solvent, through column Chromatography obtains sulfoxide compound shown in formula (I).
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Cited By (3)

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CN110256307A (en) * 2019-06-27 2019-09-20 南京雷正医药科技有限公司 A method of synthesis sulfoxide compound
CN113737206A (en) * 2021-09-16 2021-12-03 青岛科技大学 Synthesis method for preparing sulfoxide compound from thioether under electrochemistry
CN115385831A (en) * 2022-08-31 2022-11-25 浙江工业大学 Method for preparing alkyne sulfone compound by oxidation of selenium-containing catalytic system

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110256307A (en) * 2019-06-27 2019-09-20 南京雷正医药科技有限公司 A method of synthesis sulfoxide compound
CN110256307B (en) * 2019-06-27 2021-01-29 南京雷正医药科技有限公司 Method for synthesizing sulfoxide compound
CN113737206A (en) * 2021-09-16 2021-12-03 青岛科技大学 Synthesis method for preparing sulfoxide compound from thioether under electrochemistry
CN115385831A (en) * 2022-08-31 2022-11-25 浙江工业大学 Method for preparing alkyne sulfone compound by oxidation of selenium-containing catalytic system
CN115385831B (en) * 2022-08-31 2023-11-10 浙江工业大学 Method for preparing alkyne sulfone compound by oxidation of selenium-containing catalytic system

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Application publication date: 20180904