CN107602501A - The synthetic method of the ketone of 1,2 benzisothiazole of N normal-butyls 3 - Google Patents
The synthetic method of the ketone of 1,2 benzisothiazole of N normal-butyls 3 Download PDFInfo
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Abstract
The present invention relates to chemical field, discloses a kind of synthetic method of the ketone of 1,2 benzisothiazole of N normal-butyls 3, including：S1：In organic solvent, acyl chloride reaction is occurred into for methylmercapto benzoic acid and acyl chlorides agent, obtains methylmercapto chlorobenzoyl chloride；S2：Methylmercapto chlorobenzoyl chloride is dissolved in organic solvent, amidation process occurs for the mixture for adding n-butylamine and organic solvent, obtains N normal-butyl methylmercapto benzamides；S3：N normal-butyl methylmercapto benzamides are dissolved in water, hydrogen peroxide is added thereto and carries out oxidation reaction, obtain N normal-butyl methylmercapto benzamide oxides；S4：In organic solvent, ring-closure reaction is occurred into for N normal-butyls methylmercapto benzamide oxide and acyl chlorides agent, obtains the ketone of 1,2 benzisothiazole of N normal-butyls 3.The present invention can effectively avoid the generation of O-substitutive derivative, and ring-closure reaction is easily carried out, and purpose product generation is easy, and cost is cheap.
Description
Technical field
The present invention relates to chemical field, more particularly to a kind of synthesis side of N- normal-butyls-BIT
Method.
Background technology
1.2- benzisothiazole-3-ketone（Hereinafter referred to as BIT）Derivative be usually H above N atoms by alkyl-R
Or benzyl-CH2Ar carries out the product after substitution reaction, and principal item has：N- normal-butyl -1,2- benzisothiazole-3-ketones
（Hereinafter referred to as BBIT）, N- benzyls【Adjacent chlorine（Bromine）- phenyl】- 1.2- benzisothiazole-3-ketones, N- benzyls【M-chloro（Bromine）- benzene
Base】- 1.2- benzisothiazole-3-ketones, N- benzyls【To chlorine（Bromine）- phenyl】- 1.2- benzisothiazole-3-ketones, N- benzyls
（O-methoxy-phenyl）- 1.2- benzisothiazole-3-ketones, N- benzyls（Meta-methoxy-phenyl）- 1.2- benzisothiazoles-
3- ketone, N- benzyls（To methoxyl group-phenyl）- 1.2- benzisothiazole-3-ketones.
Wherein BBIT is oil-soluble wide-spectrum bactericide, has bactericidal activity, for protecting PVC, polyurethane, silica gel tree
The condensates such as fat, polyolefin, polyester can give surface-active to provide plastics and painting from bacterium, mould, the erosion of algae
Expect the effect of dry film antibacterial surface.
CL, Br ,-OCH are carried on phenyl ring3Benzyl substitution product can be with synthetic antimicrobial, anti-inflammatory, antiviral drug.
BBIT is typically to represent in above-mentioned Product formation, in addition to required N-for product, also produces 15% ~ 28%
O-for product.For example, at present synthesis BBIT mainly using BIT as primary raw material in the basic conditions with chlorobutane or NBB
Condensation reaction is carried out, chemical reaction process is as follows：
,
Because BIT can form BIT sodium salt in the basic conditions, enol covibration be present, produce sodium phenolate, course of reaction is such as
Under：
,
Therefore BIT and chlorobutane be when carrying out condensation reaction, generate O-structured product, and caused amount is with the rise of temperature,
The enhancing of alkalescence, caused amount increase therewith.N-structure accounts for 70% ~ 85% in above-mentioned reaction product；O-structure accounts for 15% ~ 30%,
Its separation method annoyings the application of the -substituted derivatives of BIT always.
Foreign countries have the product that Patents report is played to BIT with neoprene or NBB is condensed to be separated using rectification method（Patent
Application number：US8884024B1）, but the requirement to equipment is high, such as requires that its absolute pressure must be down to 30Pa or so, at present
Vacuum equipment can not meet requirement.Also have been reported that and iodate is used to BIT and the condensation of substituted benzyl aromatic compound product
Lithium makees catalyst（Number of patent application：200910197261.6 applicant：Shanghai KaiTuoZhe Chemical Research Management Co., Ltd）,
O is set to be changed into N for structure for structured product, but anhydrous lithium iodide is expensive, and production cost is high.Patent No.
A kind of 201410003853.0 Chinese patent, entitled synthetic method of 2- butyl-BIT, makes
It is raw material with methylmercapto benzoic acid, acyl chloride reaction occurs with acyl chlorides agent, methylmercapto chlorobenzoyl chloride is obtained, then by adjacent first sulphur
With n-butylamine amidation process occurs for base chlorobenzoyl chloride, corresponding amide compound is obtained, finally by amide compound and halogenation
Ring-closure reaction occurs for agent, obtains purpose product 2- butyl-BIT, derives although avoiding O-substitution
The generation of thing, but the halogenating agent used in the patent is bromine, it is expensive, and final step ring-closure reaction is not easy to carry out,
Purpose product generation is difficult.
The content of the invention
Goal of the invention：For problems of the prior art, the present invention provides a kind of N- normal-butyls -1,2- benzisothia
The synthetic method of oxazoline -3- ketone, the generation of O-substitutive derivative can be effectively avoided, and ring-closure reaction is easily carried out, purpose
Product generation is easy, and cost is cheap.
Technical scheme：The invention provides a kind of synthetic method of N- normal-butyls-BIT, bag
Include following steps：S1：In organic solvent, acyl chloride reaction is occurred into for methylmercapto benzoic acid and acyl chlorides agent, obtains methylmercapto
Chlorobenzoyl chloride；S2：Methylmercapto chlorobenzoyl chloride is dissolved in organic solvent, adds the mixing of n-butylamine and organic solvent thereto
Amidation process occurs for thing, obtains N- normal-butyl methylmercapto benzamides；S3：N- normal-butyl methylmercapto benzamides are dissolved in
Water, hydrogen peroxide is added thereto and carries out oxidation reaction, obtains N- normal-butyl methylmercapto benzamide oxides；S4：Organic molten
In agent, ring-closure reaction is occurred into for N- normal-butyls methylmercapto benzamide oxide and acyl chlorides agent, obtains N- normal-butyl -1,2- benzos
Isothiazoline -3- ketone.
Preferably, in the S1, methylmercapto benzoic acid and acyl chlorides agent is added into organic solvent, is warming up to 60 ~ 70
DEG C, untill reacting when the content of the methylmercapto benzoic acid in reaction solution≤0.5%, the organic solvent is sloughed, is obtained described
Methylmercapto chlorobenzoyl chloride.
Further, in the S2, methylmercapto chlorobenzoyl chloride is added into organic solvent, is added dropwise thereto at room temperature
The mixture of n-butylamine and organic solvent, 80 ~ 90 DEG C of 1.5 ~ 2.5h of reaction are warming up to, adjust the pH value of reaction solution to 7 ~ 7.5,
Unnecessary n-butylamine and organic solvent are distilled to recover, the N- normal-butyls methylmercapto benzamide is obtained after washing, filtering.
Preferably, in the S3, after N- normal-butyl methylmercapto benzamides are dissolved in into water, first by the aqueous solution liter
Then hydrogen peroxide insulation reaction, the N- normal-butyl methylmercapto benzoyls into reaction solution is added dropwise to 45 ~ 55 DEG C in temperature thereto
Untill during the content of amine≤1.0%, 25 ~ 35 DEG C are cooled to, filtering, obtains the N- normal-butyls methylmercapto benzamide oxide.
Preferably, in the S4, N- normal-butyl methylmercapto benzamide oxides, heating are added in organic solvent
Dehydration, and with 50 ~ 60 DEG C of dropwise addition acyl chlorides agent, the N- normal-butyl neighbour's first sulphur being warming up in 75 ~ 85 DEG C of back flow reaction to reaction solutions
Untill during yl-benzamide oxide content≤1.06%, normal pressure recovery organic solvent and excessive acyl chlorides agent, it is evaporated under reduced pressure to
N- normal-butyl -1,2- benzisothiazole-3-ketones.
Preferably, in the S1 and S2, the organic solvent is dichloroethanes, in the S4, the organic solvent
For benzene.
Preferably, the acyl chlorides agent is thionyl chloride.
Preferably, in the S1, the mass ratio of the methylmercapto benzoic acid and the thionyl chloride is 1.1 ~ 1.3:
1；And/or in the S2, the mass ratio of the methylmercapto chlorobenzoyl chloride and the n-butylamine is 1 ~ 1.2:1；And/or
In the S3, the mass ratio of the N- normal-butyls methylmercapto benzamide and the hydrogen peroxide is 1.2 ~ 1.6:1；And/or
In the S4, the mass ratio of the N- normal-butyls methylmercapto benzamide oxide and the thionyl chloride is 1.5 ~ 1.8:1.
Beneficial effect：From methylmercapto benzoic acid be raw material in the present invention, first with acyl chlorides agent（It is preferred that use protochloride
Sulfone）Generation acyl chloride reaction, obtains methylmercapto chlorobenzoyl chloride, and course of reaction is as follows：
,
Then with n-butylamine amidation process occurs for methylmercapto chlorobenzoyl chloride again, obtains N- normal-butyl methylmercapto benzamides,
Course of reaction is as follows：
,
Then hydrogen peroxide oxidation N- normal-butyl methylmercapto benzamides are used, the oxidation reaction process of generation is as follows：
,
Finally, by N- normal-butyls methylmercapto benzamide oxide and acyl chlorides agent（It is preferred that use thionyl chloride）Generation closed loop is anti-
Should, N- normal-butyls-BIT is obtained, course of reaction is as follows：
Because the present invention from methylmercapto benzoic acid is raw material, avoid using BIT, in the absence of enol covibration, so as to
Enough generations for effectively avoiding O-substitutive derivative, using methylmercapto benzoic acid successively with thionyl chloride " chloride is anti-
Should ", after the amidation process of n-butylamine, using hydrogen peroxide oxidation N- normal-butyl methylmercapto benzamides, generation hasStructure N- normal-butyl methylmercapto benzamide oxides, relative toStructure
N- normal-butyl methylmercapto benzamides, due to reducing the cloud density of S atom, and be easier to occur with thionyl chloride
Ring-closure reaction, while generate stable chlorosulfuric acid and purpose product N- normal-butyls-BIT.
Embodiment
The present invention is described in detail with reference to specific embodiment.
Embodiment 1：
Methylmercapto benzoic acid, the 41g thionyl chlorides that 0.30mol about 50.4g are dried, heating are added into 200ml dichloroethanes
To 60 DEG C, after reacting a period of time, gas-chromatography HPLC completes acyl chlorides when analyzing unreacted methylmercapto benzoic acid≤0.50%
Change reaction.Solvent dichloroethanes is sloughed, obtains methylmercapto chlorobenzoyl chloride 53.7g, yield 96.0%.Contain in HPLC analysis products
Methylmercapto chlorobenzoyl chloride 99.54%, methylmercapto benzoic acid 0.46%.
Into 300ml dichloroethanes add 0.30mol about 55.9g methylmercapto chlorobenzoyl chlorides, be added dropwise at room temperature by
The mixtures of 50.4g n-butylamines and 50g dichloroethanes composition, 80 DEG C of reaction 2h of heating are added, add soda ash 18.5g, water 50g,
Unnecessary n-butylamine, dichloroethanes are distilled to recover, washes, filter to obtain solid N- normal-butyl methylmercapto benzamides 63.2g.
Contain N- normal-butyl methylmercaptos benzamide 99.26%, yield 94.6% in HPLC analysis products.
0.30mol about 66.9gN- normal-butyl methylmercapto benzamides are added in 120ml water, are warming up to 50 DEG C, drop
The hydrogen peroxide that the mass fraction for adding about 44.2g is 30%, adds insulation reaction 1h, and sampling carries out HPLC analyses, do not aoxidize original
Material --- oxidation reaction is completed during i.e. unreacted N- normal-butyls methylmercapto benzamide≤1.0%, cools to 30 DEG C, is filtered,
Solid 76.3g, solid content 86% are obtained, HPLC analyses wherein contain N- normal-butyl methylmercapto benzamides oxide 99.38%, received
Rate 91.52%.
0.30mol about 71.7g N- normal-butyl methylmercapto benzamide oxides, heating are added into 300ml benzene
Dehydration；Thionyl chloride about 42.5g is added dropwise in 55 DEG C, adds 80 DEG C of heating back flow reaction 2 hours, sampling carries out HPLC analyses, instead
Answer and contain N- normal-butyls-BIT 98.74%, non-closed loop thing 1.06% in thing；Normal pressure reclaims benzene and excess
Thionyl chloride, be evaporated under reduced pressure, obtain N- normal-butyls-BIT 58.9g, HPLC analysis N- normal-butyl -1,
The content of 2- benzisothiazole-3-ketones is 98.76%, yield 94.85%.
Embodiment 2：
Methylmercapto benzoic acid, the 52g thionyl chlorides that 0.34mol about 58.1g are dried, heating are added into 200ml dichloroethanes
To 61 DEG C, after reacting a period of time, gas-chromatography HPLC completes acyl chlorides when analyzing unreacted methylmercapto benzoic acid≤0.50%
Change reaction.Desolventizing, obtain methylmercapto chlorobenzoyl chloride 62.1g, yield 96.3%.Contain methylmercapto benzene in HPLC analysis products
Formyl chloride 99.60%, methylmercapto benzoic acid 0.39%.
Into 300ml dichloroethanes add 0.31mol about 58.4g methylmercapto chlorobenzoyl chlorides, be added dropwise at room temperature by
The mixture of 52.4g n-butylamines and 52g dichloroethanes composition, 82 DEG C of reaction 2.5h of heating are added, add soda ash 23.1g, water
60g, unnecessary n-butylamine, dichloroethanes are distilled to recover, wash, filter to obtain solid N- normal-butyl methylmercapto benzamides
66.3g.Contain N- normal-butyl methylmercaptos benzamide 99.31%, yield 94.9% in HPLC analysis products.
0.34mol about 75.8gN- normal-butyl methylmercapto benzamides are added in 130ml water, are warming up to 50 DEG C, drop
The hydrogen peroxide that the mass fraction for adding about 54.0g is 30%, adds insulation reaction 1h, and sampling carries out HPLC analyses, do not aoxidize original
Material --- oxidation reaction is completed during i.e. unreacted N- normal-butyls methylmercapto benzamide≤1.0%, cools to 30 DEG C, is filtered,
Solid 87.8g, solid content 85% are obtained, HPLC analyses wherein contain N- normal-butyl methylmercapto benzamides oxide 99.47%, received
Rate 91.86%.
0.34mol about 80.7g N- normal-butyl methylmercapto benzamide oxides, heating are added into 300ml benzene
Dehydration；Thionyl chloride about 46.7g is added dropwise in 55 DEG C, adds 80 DEG C of heating back flow reaction 2 hours, sampling carries out HPLC analyses, instead
Answer and contain N- normal-butyls-BIT 98.70%, non-closed loop thing 1.23% in thing；Normal pressure reclaims benzene and excess
Thionyl chloride, be evaporated under reduced pressure, obtain N- normal-butyls-BIT 65.8g, HPLC analysis N- normal-butyl -1,
The content of 2- benzisothiazole-3-ketones is 98.76%, yield 94.14%.
Embodiment 3：
Methylmercapto benzoic acid, the 48g thionyl chlorides that 0.36mol about 61.2g are dried, heating are added into 200ml dichloroethanes
To 62 DEG C, after reacting a period of time, gas-chromatography HPLC completes acyl chlorides when analyzing unreacted methylmercapto benzoic acid≤0.50%
Change reaction.Desolventizing, obtain methylmercapto chlorobenzoyl chloride 64.3g, yield 94.7%.Contain methylmercapto benzene in HPLC analysis products
Formyl chloride 99.44%, methylmercapto benzoic acid 0.55%.
Into 300ml dichloroethanes add 0.33mol about 61.5g methylmercapto chlorobenzoyl chlorides, be added dropwise at room temperature by
The mixture of 55.0g n-butylamines and 55g dichloroethanes composition, 81 DEG C of reaction 2.2h of heating are added, add soda ash 24.5g, water
75g, unnecessary n-butylamine, dichloroethanes are distilled to recover, wash, filter to obtain solid N- normal-butyl methylmercapto benzamides
69.1g.Contain N- normal-butyl methylmercaptos benzamide 99.06%, yield 94.0% in HPLC analysis products.
0.29mol about 64.2gN- normal-butyl methylmercapto benzamides are added in 120ml water, are warming up to 50 DEG C, drop
The hydrogen peroxide that the mass fraction for adding about 48.4g is 30%, adds insulation reaction 1h, and sampling carries out HPLC analyses, do not aoxidize original
Material --- oxidation reaction is completed during i.e. unreacted N- normal-butyls methylmercapto benzamide≤1.0%, cools to 30 DEG C, is filtered,
Solid 73.7g, solid content 86% are obtained, HPLC analyses wherein contain N- normal-butyl methylmercapto benzamides oxide 99.50%, received
Rate 92.07%.
0.34mol about 80.4g N- normal-butyl methylmercapto benzamide oxides, heating are added into 300ml benzene
Dehydration；Thionyl chloride about 52.0g is added dropwise in 55 DEG C, adds 80 DEG C of heating back flow reaction 2 hours, sampling carries out HPLC analyses, instead
Answer and contain N- normal-butyls-BIT 98.89%, non-closed loop thing 0.92% in thing；Normal pressure reclaims benzene and excess
Thionyl chloride, be evaporated under reduced pressure, obtain N- normal-butyls-BIT 66.25g, HPLC analysis N- normal-butyls-
The content of BIT is 99.04%, yield 95.15%.
The technical concepts and features of above-mentioned embodiment only to illustrate the invention, its object is to allow be familiar with technique
People can understand present disclosure and implement according to this, and it is not intended to limit the scope of the present invention.It is all according to the present invention
The equivalent transformation or modification that Spirit Essence is done, should all be included within the scope of the present invention.
Claims (8)
1. a kind of synthetic method of N- normal-butyls-BIT, it is characterised in that comprise the following steps：
S1：In organic solvent, acyl chloride reaction is occurred into for methylmercapto benzoic acid and acyl chlorides agent, obtains methylmercapto benzoyl
Chlorine；
S2：Methylmercapto chlorobenzoyl chloride is dissolved in organic solvent, the mixture for adding n-butylamine and organic solvent thereto is sent out
Raw amidation process, obtains N- normal-butyl methylmercapto benzamides；
S3：N- normal-butyl methylmercapto benzamides are dissolved in water, hydrogen peroxide is added thereto and carries out oxidation reaction, obtain the positive fourths of N-
Base methylmercapto benzamide oxide；
S4：In organic solvent, ring-closure reaction is occurred into for N- normal-butyls methylmercapto benzamide oxide and acyl chlorides agent, obtains N-
Normal-butyl-BIT.
2. the synthetic method of N- normal-butyls-BIT according to claim 1, it is characterised in that
In the S1, methylmercapto benzoic acid and acyl chlorides agent are added into organic solvent, is warming up to 60 ~ 70 DEG C, reaction is to reacting molten
Untill during the content of the methylmercapto benzoic acid in liquid≤0.5%, the organic solvent is sloughed, obtains the methylmercapto benzoyl
Chlorine.
3. the synthetic method of N- normal-butyls-BIT according to claim 1, it is characterised in that
In the S2, methylmercapto chlorobenzoyl chloride is added into organic solvent, n-butylamine and organic solvent is added dropwise thereto at room temperature
Mixture, be warming up to 80 ~ 90 DEG C of 1.5 ~ 2.5h of reaction, adjust the pH value of reaction solution to 7 ~ 7.5, be distilled to recover it is unnecessary just
Butylamine and organic solvent, the N- normal-butyls methylmercapto benzamide is obtained after washing, filtering.
4. the synthetic method of N- normal-butyls-BIT according to claim 1, it is characterised in that
In the S3, after N- normal-butyl methylmercapto benzamides are dissolved in into water, the aqueous solution is first warming up to 45 ~ 55 DEG C, so
Hydrogen peroxide insulation reaction, content≤1.0% of the N- normal-butyl methylmercapto benzamides into reaction solution is added dropwise thereto afterwards
When untill, be cooled to 25 ~ 35 DEG C, filtering, obtain the N- normal-butyls methylmercapto benzamide oxide.
5. the synthetic method of N- normal-butyls-BIT according to claim 1, its feature exist
In, in the S4, add N- normal-butyl methylmercapto benzamide oxides in organic solvent, heating dehydration, and with 50 ~
60 DEG C of dropwise addition acyl chlorides agent, the N- normal-butyl methylmercapto benzamide oxygen being warming up in 75 ~ 85 DEG C of back flow reaction to reaction solutions
Untill during compound content≤1.06%, normal pressure recovery organic solvent and excessive acyl chlorides agent, N- normal-butyl -1 is evaporated under reduced pressure to,
2- benzisothiazole-3-ketones.
6. the synthetic method of N- normal-butyls-BIT according to any one of claim 1 to 5,
Characterized in that, in the S1 and S2, the organic solvent is dichloroethanes, and in the S4, the organic solvent is benzene.
7. the synthetic method of N- normal-butyls-BIT according to any one of claim 1 to 5,
Characterized in that, the acyl chlorides agent is thionyl chloride.
8. the synthetic method of N- normal-butyls-BIT according to claim 7, it is characterised in that
In the S1, the mass ratio of the methylmercapto benzoic acid and the thionyl chloride is 1.1 ~ 1.3:1；
And/or in the S2, the mass ratio of the methylmercapto chlorobenzoyl chloride and the n-butylamine is 1 ~ 1.2:1；
And/or in the S3, the mass ratio of the N- normal-butyls methylmercapto benzamide and the hydrogen peroxide for 1.2 ~
1.6:1；
And/or in the S4, the mass ratio of the N- normal-butyls methylmercapto benzamide oxide and the thionyl chloride
For 1.5 ~ 1.8:1.
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| CN108822055A (en) * | 2018-05-07 | 2018-11-16 | 常州大学 | A kind of new method of 2- butyl -1,2- benzisothiazole-3-ketone |
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| CN112625000A (en) * | 2020-12-04 | 2021-04-09 | 大丰跃龙化学有限公司 | Synthesis method of N-alkane-1, 2-benzisothiazolin-3-ketone |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108822055A (en) * | 2018-05-07 | 2018-11-16 | 常州大学 | A kind of new method of 2- butyl -1,2- benzisothiazole-3-ketone |
| CN111253335A (en) * | 2020-03-12 | 2020-06-09 | 浙江扬帆新材料股份有限公司 | Novel synthesis method of N-substituted benzisothiazolin-3-one derivative |
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| CN112625000A (en) * | 2020-12-04 | 2021-04-09 | 大丰跃龙化学有限公司 | Synthesis method of N-alkane-1, 2-benzisothiazolin-3-ketone |
| CN112624999A (en) * | 2020-12-04 | 2021-04-09 | 大丰跃龙化学有限公司 | 1, 2-benzisothiazolin-3-one solid waste after-treatment process |
| CN112625000B (en) * | 2020-12-04 | 2023-05-26 | 安徽屹墩科技股份有限公司 | Synthesis method of N-alkane-1, 2-benzisothiazolin-3-one |
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