JP2005112810A5 - - Google Patents
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- JP2005112810A5 JP2005112810A5 JP2003350882A JP2003350882A JP2005112810A5 JP 2005112810 A5 JP2005112810 A5 JP 2005112810A5 JP 2003350882 A JP2003350882 A JP 2003350882A JP 2003350882 A JP2003350882 A JP 2003350882A JP 2005112810 A5 JP2005112810 A5 JP 2005112810A5
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- difluoromethyl
- benzyl
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- -1 benzyl (difluoromethyl) sulfide compound Chemical class 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- 150000004714 phosphonium salts Chemical group 0.000 claims description 3
- 150000003983 crown ethers Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- QMOWRNGLGDZHAF-UHFFFAOYSA-N difluoromethylsulfanylmethylbenzene Chemical compound FC(F)SCC1=CC=CC=C1 QMOWRNGLGDZHAF-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QXGDJMRRBRQFBI-UHFFFAOYSA-N phenylmethanethiol;potassium Chemical compound [K].SCC1=CC=CC=C1 QXGDJMRRBRQFBI-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
ジフルオロメチルスルホニルアニリド誘導体のあるものは除草剤として有用であることが知られている。本発明はジフルオロメチルスルホニル基の導入に用いるジフルオロメチルスルホニルクロライドを製造する際に、前駆体として有用なベンジル（ジフルオロメチル）スルフィド化合物を製造する方法に関するものである。 Certain difluoromethylsulfonylanilide derivatives are known to be useful as herbicides. The present invention is in the production difluoromethyl sul ho Nirukuroraido used for introduction of the difluoromethyl sulfonyl group, to a method for producing a useful benzyl (difluoromethyl) sulfide compound as a precursor.
本発明は、下記〔１〕乃至〔９〕項に記載の発明を提供する事により前記課題を解決したものである。
〔１〕一般式（１）
This invention solves the said subject by providing the invention as described in the following [1] thru | or [ 9 ] item.
[1] General formula (1)
〔４〕Ｘ２が塩素原子である、〔１〕ないし〔３〕のいずれか１項に記載のベンジル（ジフルオロメチル）スルフィド化合物の製造方法。 [4] The method for producing a benzyl (difluoromethyl) sulfide compound according to any one of [1] to [ 3 ], wherein X 2 is a chlorine atom.
〔５〕Ｘ１がアルカリ金属である、〔１〕乃至〔４〕のいずれか１項に記載のベンジル（ジフルオロメチル）スルフィド化合物の製造方法。 [5 ] The method for producing a benzyl (difluoromethyl) sulfide compound according to any one of [1] to [4], wherein X 1 is an alkali metal.
〔６〕有機層が芳香族炭化水素、脂肪族炭化水素、ハロゲン化炭化水素、脂環式炭化水素、エーテル系溶媒、又はエステル系溶媒のいずれかを含むものである、〔１〕乃至〔５〕のいずれか１項に記載のベンジル（ジフルオロメチル）スルフィド化合物の製造方法。 [6] The organic layer contains any one of an aromatic hydrocarbon, an aliphatic hydrocarbon, a halogenated hydrocarbon, an alicyclic hydrocarbon, an ether solvent, or an ester solvent, [1] to [ 5 ] The manufacturing method of the benzyl (difluoromethyl) sulfide compound of any one of Claims.
〔７〕有機層が芳香族炭化水素を含むものである、〔１〕乃至〔５〕のいずれか１項に記載のベンジル（ジフルオロメチル）スルフィド化合物の製造方法。 [7] The method for producing a benzyl (difluoromethyl) sulfide compound according to any one of [1] to [ 5 ], wherein the organic layer contains an aromatic hydrocarbon.
〔８〕相間移動触媒が四級アンモニウム塩、四級ホスホニウム塩、クラウンエーテル類、ポリエチレングリコール類である、〔２〕乃至〔７〕項のいずれか１項に記載のベンジル（ジフルオロメチル）スルフィド化合物の製造方法。 [8] The benzyl (difluoromethyl) sulfide compound according to any one of [ 2 ] to [ 7 ], wherein the phase transfer catalyst is a quaternary ammonium salt, a quaternary phosphonium salt, a crown ether, or a polyethylene glycol. Manufacturing method.
〔９〕相間移動触媒が四級アンモニウム塩である、〔２〕乃至〔７〕のいずれか１項に記載のベンジル（ジフルオロメチル）スルフィド化合物の製造方法。 [9] The method for producing a benzyl (difluoromethyl) sulfide compound according to any one of [ 2 ] to [ 7 ], wherein the phase transfer catalyst is a quaternary ammonium salt.
当反応は相間移動触媒を用いずとも反応が進行するものであるが、反応速度や目的物収率を高めるといった観点からは相間移動触媒を用いることが好ましい。当反応に用いうる相間移動触媒としては、相間移動触媒として機能しうる化合物であれば差し支えないが、例えば、テトラブチルアンモニウムブロミド、トリ−ｎ−オクチルメチルアンモニウムクロリド（株式会社 同仁科学研究所から「カプリコート」なる商品名で市販されている。）、テトラブチルアンモニウムクロリド等の四級アンモニウム塩；テトラフェニルホスホニウムブロミド、テトラフェニルホスホニウムクロリド等の四級ホスホニウム塩；１８−クラウン−６、ジベンゾ−１８−クラウン−６等のクラウンエーテル類；ＰＥＧ−３００（数平均分子量３００のポリエチレングリコール）、ＰＥＧ−４００（数平均分子量４００のポリエチレングリコール）、ＰＥＧ−６００（数平均分子量６００のポリエチレングリコール）等のポリエチレングリコール類を例示することができるが、好ましくは四級アンモニウム塩を用いるのが良く、特に好ましくはテトラブチルアンモニウムブロミドを用いて行なうのがよい。 Although this reaction proceeds without using a phase transfer catalyst, it is preferable to use a phase transfer catalyst from the viewpoint of increasing the reaction rate and the yield of the target product. The phase transfer catalyst that can be used for this reaction is not limited as long as it is a compound that can function as a phase transfer catalyst. Quaternary ammonium salts such as tetrabutylammonium chloride; quaternary phosphonium salts such as tetraphenylphosphonium bromide and tetraphenylphosphonium chloride; 18-crown-6, dibenzo-18 - crown ethers such as crown; (polyethylene glycol having a number average molecular weight 300) PEG-300, (polyethylene glycol having a number average molecular weight of 400) PEG-400, PEG- 600 ( polyethylene glycol having a number average molecular weight of 6 00) It can be exemplified polyethylene glycols, preferably better to use a quaternary ammonium salt, particularly preferably may be carried out using tetrabutylammonium bromide.
反応器への原料等の添加順序及び反応方法は特に制限されないが、好適な例としては、水及び有機層中に相間移動触媒を加え、これにベンジルメルカプタン化合物を加え溶解させ、次いで、ハロゲン化ジフルオロメタンを導入することにより反応を行い、ベンジル（ジフルオロメチル）フルフィド化合物を得る方法が挙げられる。 Order of addition and reaction methods raw materials to the reactor is not particularly limited, suitable examples include a phase transfer catalyst was added to the aqueous and organic layers, this was dissolved by adding benzyl mercaptan compound and then, halogen A method of reacting by introducing difluoromethane to obtain a benzyl (difluoromethyl) fluoride compound is mentioned.
反応終了後、有機層に抽出されている一般式（３）で表されるベンジル（ジフルオロメチル）スルフィド化合物は単離することなく溶液のままを他の反応に用いることもできるし、蒸留などにより一般式（３）で表されるベンジル（ジフルオロメチル）フルフィド化合物を単離することもできる。 After completion of the reaction, benzyl (difluoromethyl) S Rufido compound represented by the general formula (3), which is extracted into the organic layer can either be used remains of the solution to the other reaction without isolation, distillation, etc. The benzyl (difluoromethyl) fluoride compound represented by the general formula (3) can also be isolated.
当反応によれば、相間移動触媒存在下、有機層と水の二層系で反応し、一般式（３）で表されるベンジル（ジフルオロメチル）スルフィド化合物が生成する。得られる一般式（３）で表されるベンジル（ジフルオロメチル）スルフィド化合物は、ジフルオロメチルフルホニルクロライドの前駆体として有用な化合物である。 According to those reaction, a phase transfer catalyst presence, reacted in a two-layer system of an organic layer and an aqueous, benzyl (difluoromethyl) S Rufido compound represented by the general formula (3) is produced. Benzyl represented by the resulting formula (3) (difluoromethyl) S Rufido compound is a compound useful as a precursor of difluoromethyl full Honi chloride.
次に、実施例を挙げて本発明の製造方法を具体的に説明するが、本発明は、これら実施例によって何ら限定されるものではない。 Next, a detailed explanation of the manufacturing method of the present onset bright to examples, the present invention is not intended to be limited to these examples.
次いで、クロロジフルオロメタン１０．０ｇを４時間かけて導入し、４８％水酸化カリウム水溶液１１．６ｇ（０．１ｍｏｌ）を加えた。クロロジフルオロメタン２．７ｇを４０分かけて導入し反応した。反応終了後、水５０ｍｌを加え分液した。有機層を更に水２５ｍｌで洗浄し、ベンジル（ジフルオロメチル）スルフィドのトルエン溶液を５４．８ｇ（収率８８．４％）得た。 Next, 10.0 g of chlorodifluoromethane was introduced over 4 hours, and 11.6 g (0.1 mol) of a 48% aqueous potassium hydroxide solution was added. 2.7 g of chlorodifluoromethane was introduced over 40 minutes to react. After completion of the reaction, 50 ml of water was added for liquid separation. The organic layer was further washed with 25 ml of water to obtain 54.8 g (yield: 88.4% ) of a toluene solution of benzyl (difluoromethyl) sulfide.
次いで、クロロジフルオロメタン１０．０ｇを４．５時間かけて導入し、４８％水酸化カリウム水溶液１１．６ｇ（０．１ｍｏｌ）を加えた。クロロジフルオロメタン２．７ｇを１時間かけて導入し反応した。反応終了後、水５０ｍｌを加え分液した。有機層を更に水２５ｍｌで洗浄し、ベンジル（ジフルオロメチル）スルフィドのキシレン溶液を６２．４ｇ（収率８６．８％）得た。 Next, 10.0 g of chlorodifluoromethane was introduced over 4.5 hours, and 11.6 g (0.1 mol) of a 48% aqueous potassium hydroxide solution was added. 2.7 g of chlorodifluoromethane was introduced and reacted over 1 hour. After completion of the reaction, 50 ml of water was added for liquid separation. The organic layer was further washed with 25 ml of water to obtain 62.4 g (yield: 86.8% ) of a xylene solution of benzyl (difluoromethyl) sulfide.
次いでクロロジフルオロメタン１０．０ｇを２．５時間かけて導入し、４８％水酸化カリウム水溶液１１．６ｇ（０．１ｍｏｌ）を加えた。クロロジフルオロメタン２．７ｇを４０分かけて導入し反応した。反応終了後、水５０ｍｌを加え分液した。有機層を更に水２５ｍｌで洗浄し、ベンジル（ジフルオロメチル）スルフィドのクロロベンゼン溶液を７６.０ｇ（収率８２.９％）得た。 Next, 10.0 g of chlorodifluoromethane was introduced over 2.5 hours, and 11.6 g (0.1 mol) of a 48% aqueous potassium hydroxide solution was added. 2.7 g of chlorodifluoromethane was introduced over 40 minutes to react. After completion of the reaction, 50 ml of water was added for liquid separation. The organic layer was further washed with 25 ml of water to obtain 76.0 g (yield 82.9% ) of a chlorobenzene solution of benzyl (difluoromethyl) sulfide.
次いで、クロロジフルオロメタン１５．０ｇを５時間かけて導入し、４８％水酸化カリウム水溶液１１．６ｇ（０．１ｍｏｌ）を加えた。クロロジフルオロメタン７．７ｇを４時間かけて導入し反応した。反応終了後、水５０ｍｌを加え分液した。有機層を更に水２５ｍｌで洗浄し、ベンジル（ジフルオロメチル）スルフィドのクロロベンゼン溶液を６４.６ｇ（収率４５．０％）得た。 Next, 15.0 g of chlorodifluoromethane was introduced over 5 hours, and 11.6 g (0.1 mol) of a 48% aqueous potassium hydroxide solution was added. 7.7 g of chlorodifluoromethane was introduced over 4 hours to react. After completion of the reaction, 50 ml of water was added for liquid separation. The organic layer was further washed with 25 ml of water to obtain 64.6 g (yield: 45.0% ) of a chlorobenzene solution of benzyl (difluoromethyl) sulfide.
実施例７：ベンジル（ジフルオロメチル）スルフィドの合成
２００ｍｌの四径フラスコに水５０ｍｌ、クロロベンゼン５０ｍｌを加え、水酸化カリウム２８．１ｇ（０．５ｍｏｌ）、ＰＥＧ−４００を０.９０ｇ加えた。窒素雰囲気下、攪拌しながら６０℃まで昇温した。ベンジルチオロニウム塩酸塩２０．４ｇ（０．１ｍｏｌ）を加え、４０分熟成した後、４０℃まで冷却し、ベンジルメルカプタンカリウム塩を系内で調製した。
Example 7: Benzyl (difluoromethyl) water 50ml four-neck flask Synthesis 200ml sulfide, chlorobenzene 50ml was added, potassium hydroxide 28.1 g (0.5 mol), the PEG-400 was e 0.90 g pressurized. The temperature was raised to 60 ° C. with stirring in a nitrogen atmosphere. After adding 20.4 g (0.1 mol) of benzylthioronium hydrochloride and aging for 40 minutes, the mixture was cooled to 40 ° C. to prepare benzyl mercaptan potassium salt in the system.
次いで、クロロジフルオロメタン１５．０ｇを１２時間かけて導入し、４８％水酸化カリウム水溶液１１．６ｇ（０．１ｍｏｌ）を加えた。クロロジフルオロメタン４.２ｇを６時間かけて導入し反応した。反応終了後、水５０ｍｌ、クロロベンゼン５０ｍｌを加え分液した。有機層を更に水２５ｍｌで洗浄し、ベンジル（ジフルオロメチル）スルフィドのクロロベンゼン溶液を７２．４ｇ（収率８４．４％）得た。 Next, 15.0 g of chlorodifluoromethane was introduced over 12 hours, and 11.6 g (0.1 mol) of a 48% aqueous potassium hydroxide solution was added. The reaction was carried out by introducing 4.2 g of chlorodifluoromethane over 6 hours. After completion of the reaction, 50 ml of water and 50 ml of chlorobenzene were added for liquid separation. The organic layer was further washed with 25 ml of water to obtain 72.4 g (yield: 84.4% ) of a chlorobenzene solution of benzyl (difluoromethyl) sulfide.
次いで、クロロジフルオロメタン１１.４ｇを９時間かけて導入し反応した。反応終了後、水５０ｍｌを加え分液した。有機層を更に水２５ｍｌで洗浄し、ベンジル（ジフルオロメチル）スルフィドのクロロベンゼン溶液を６４.４ｇ（収率４５．４％）得た。 Subsequently, 11.4 g of chlorodifluoromethane was introduced over 9 hours to react. After completion of the reaction, 50 ml of water was added for liquid separation. The organic layer was further washed with 25 ml of water to obtain 64.4 g (yield 45.4% ) of a chlorobenzene solution of benzyl (difluoromethyl) sulfide.
次いで、クロロジフルオロメタン１１.２ｇを４時間かけて導入し、４８％水酸化カリウム水溶液１１．６ｇ（０．１ｍｏｌ）を加えた。クロロジフルオロメタン４.１ｇを１時間かけて導入し反応した。反応終了後、水５０ｍｌを加え分液した。有機層を更に水２５ｍｌで洗浄し、ベンジル（ジフルオロメチル）スルフィドのクロロベンゼン溶液を６５.７ｇ（収率８２．４％）得た。 Next, 11.2 g of chlorodifluoromethane was introduced over 4 hours, and 11.6 g (0.1 mol) of a 48% aqueous potassium hydroxide solution was added. The reaction was carried out by introducing 4.1 g of chlorodifluoromethane over 1 hour. After completion of the reaction, 50 ml of water was added for liquid separation. The organic layer was further washed with 25 ml of water to obtain 65.7 g (yield: 82.4% ) of a chlorobenzene solution of benzyl (difluoromethyl) sulfide.
Claims (2)
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| Application Number | Priority Date | Filing Date | Title |
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| JP2003350882A JP4465674B2 (en) | 2003-10-09 | 2003-10-09 | Method for producing benzyl (difluoromethyl) sulfide compound |
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| JP2003350882A JP4465674B2 (en) | 2003-10-09 | 2003-10-09 | Method for producing benzyl (difluoromethyl) sulfide compound |
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| Publication Number | Publication Date |
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| JP2005112810A JP2005112810A (en) | 2005-04-28 |
| JP2005112810A5 true JP2005112810A5 (en) | 2006-11-24 |
| JP4465674B2 JP4465674B2 (en) | 2010-05-19 |
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| JP2003350882A Expired - Lifetime JP4465674B2 (en) | 2003-10-09 | 2003-10-09 | Method for producing benzyl (difluoromethyl) sulfide compound |
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| JP (1) | JP4465674B2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5550568B2 (en) * | 2009-01-27 | 2014-07-16 | 国立大学法人九州大学 | Method for producing thio compound by conversion of dithiocarbamate |
| CN116063208A (en) * | 2023-02-13 | 2023-05-05 | 安徽省化工研究院 | Synthesis method of difluoromethane sulfonyl chloride |
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2003
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