JPH02258752A - Preparation of 4'-chloro-2'-trifluoromethylpropoxyacetanilide - Google Patents
Preparation of 4'-chloro-2'-trifluoromethylpropoxyacetanilideInfo
- Publication number
- JPH02258752A JPH02258752A JP1080948A JP8094889A JPH02258752A JP H02258752 A JPH02258752 A JP H02258752A JP 1080948 A JP1080948 A JP 1080948A JP 8094889 A JP8094889 A JP 8094889A JP H02258752 A JPH02258752 A JP H02258752A
- Authority
- JP
- Japan
- Prior art keywords
- sulfonic acid
- acid
- alpha
- benzene
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- PRFIIMLQPHQGOC-UHFFFAOYSA-N n-[4-chloro-2-(trifluoromethyl)phenyl]-2-propoxyacetamide Chemical compound CCCOCC(=O)NC1=CC=C(Cl)C=C1C(F)(F)F PRFIIMLQPHQGOC-UHFFFAOYSA-N 0.000 title claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000018044 dehydration Effects 0.000 claims abstract description 7
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 7
- SGUYGLMQEOSQTH-UHFFFAOYSA-N 2-propoxyacetic acid Chemical compound CCCOCC(O)=O SGUYGLMQEOSQTH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940092714 benzenesulfonic acid Drugs 0.000 claims abstract description 5
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 13
- 238000010992 reflux Methods 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 150000001555 benzenes Chemical class 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003905 agrochemical Substances 0.000 abstract 1
- -1 aniline compound Chemical class 0.000 abstract 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 abstract 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000003931 anilides Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野］
アセトアニリド（以下アニリドという、）の新規な製造
法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel method for producing acetanilide (hereinafter referred to as anilide).
−Ｃ的な置換アニリドの製造法としは、カルボン酸の酸
無水物、酸クロリド等と置換アニリンとを反応させる方
法、あるいはカルボン酸と置換゛アニリンとを縮合剤の
存在下に縮合する方法等が知られている。-C-substituted anilides can be produced by reacting a carboxylic acid anhydride, acid chloride, etc. with a substituted aniline, or by condensing a carboxylic acid and a substituted aniline in the presence of a condensing agent. It has been known.
しかしながら本発明の如く置換基としてトリフルオロメ
チル基を有する場合は、その電子吸引性のため、縮合反
応が完結しない等の問題点を有していた。However, when a trifluoromethyl group is used as a substituent as in the present invention, the condensation reaction is not completed due to its electron-withdrawing property.
本発明者等はアニリドの製造方法を種々検討した結果、
置換基を有していてもよいベンゼンスルホン酸又はナフ
タレンスルホン酸の存在下、脱水縮合し、生成する水を
連続的に系外へ出すことにより目的のアニリドが短時間
に高収率で得られることを見い出し本発明を完成した。As a result of examining various methods for producing anilide, the present inventors found that
In the presence of benzenesulfonic acid or naphthalenesulfonic acid which may have a substituent, the desired anilide can be obtained in a short time and in high yield by dehydration condensation and the produced water being continuously discharged from the system. They discovered this and completed the present invention.
（以下アニリンという、）とプロポキシ酢酸とを：ｑ
ｔａ ａを有していてもよいベンゼンスルホン酸又はナ
フタレンスルホン酸の存在下、脱水縮合させることを特
徴とするアリニドの製造法。(hereinafter referred to as aniline) and propoxyacetic acid: q
A method for producing alinide, which comprises carrying out dehydration condensation in the presence of benzenesulfonic acid or naphthalenesulfonic acid which may have ta a.
（２） 脱水縮合により生成する水を連続的に系外に
出す特許請求の範囲第１項記載の製造法である。(2) The production method according to claim 1, in which water produced by dehydration condensation is continuously discharged from the system.
反応は有機溶媒中、還流下、生成した水を共沸脱水によ
り連続的に系外へ取り出すことにより行なわれる。The reaction is carried out in an organic solvent under reflux by continuously removing the produced water from the system by azeotropic dehydration.
反応は通常、数時ＩＬ’ｌから〜】Ｏ数時間で完結する
。The reaction is usually completed within several hours.
触媒として用いる￥ｌ換ベンゼンの置換基としては低級
アルキル基、塩素原子、ニトロ基等が挙げられる。Examples of substituents on the \l-substituted benzene used as a catalyst include lower alkyl groups, chlorine atoms, and nitro groups.
有機溶媒としてはベンゼン、トルエン、キシレン等の芳
香族炭化水素、四塩化炭素、クロロホルム等のハロゲン
化炭素水素等が挙げられる。Examples of organic solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, and halogenated hydrocarbons such as carbon tetrachloride and chloroform.
反応終了後は、通常の後処理を行なうことにより目的物
を高収率で得ることができる。After the reaction is completed, the desired product can be obtained in high yield by performing usual post-treatments.
［実施例］ 次に実施例を挙げ本発明を更に詳細に説明する。[Example] Next, the present invention will be explained in more detail with reference to Examples.
実施例１
温度計、還流冷却器、共沸脱水用検水管、および撹拌機
を備えた３１フラスコにアニリン（１９６ｇ、１．０モ
ル）トルエン８００ ｇ、プロポキシ酢Ｍ（１２６ｇ、
１．０７モル）およびパラトルエンスルホン酸−水和物
１２ｇを入れ混合溶解する。Example 1 Aniline (196 g, 1.0 mol), 800 g of toluene, propoxy vinegar M (126 g,
1.07 mol) and 12 g of para-toluenesulfonic acid hydrate were added and mixed and dissolved.
内温か１１０°になるまで昇温すると還流が始まりトル
エンと共沸する水分を連続的に分液除去しながら１２時
間還流する。When the temperature is raised to an internal temperature of 110°, reflux begins and the mixture is refluxed for 12 hours while water that is azeotropic with toluene is continuously separated and removed.
反応液を冷却後、水を加え撹拌し分液しトルエン層を２
ａ縮し目的のアニリド２８７ｇ （収率９７％）を得た
。After cooling the reaction solution, water was added and stirred to separate the toluene layer.
287 g (yield: 97%) of the desired anilide was obtained by condensation.
実施例２
実施例１と同じ装置のついたフラスコにアニリン（１９
６ｇ、１．０モル）ベンゼン８００ｇ、プロポキシ酢酸
（１３６ｇ、１．１５モル）およびバ、ラドルエンスル
ホン酸−水和物１２ｇを入れ混合溶解する。昇温しベン
ゼンが還流しはしめたら共沸して出てくる水分を連続的
に分液し系外に除去しながら２５時間反応する。Example 2 Aniline (19
Add 800 g of benzene (6 g, 1.0 mol), propoxyacetic acid (136 g, 1.15 mol), and 12 g of radruenesulfonic acid hydrate and mix and dissolve. When the temperature is raised and the benzene begins to reflux, the reaction is continued for 25 hours while continuously separating and removing water produced by azeotropy from the system.
反応液、実施例１と同様に処理し、目的のアニリド２５
２ｇ （収率８５％）を得た。The reaction solution was treated in the same manner as in Example 1 to obtain the desired anilide 25.
2g (85% yield) was obtained.
実施例３
実施例１と同じ装置を備えたフラスコにアニリン（１９
６ｇ、１．０モル）トルエン８００ｇ、プロポキシ酢酸
（１２６ｇ、１．０７モル）および濃硫酸６ｇを加え’
ｆｌｌ ！’Ｐ ｉ８解する。Example 3 Aniline (19
Add 800 g of toluene (6 g, 1.0 mol), propoxyacetic acid (126 g, 1.07 mol) and 6 g of concentrated sulfuric acid.
Full! 'P i8 solve.
溶解後、トルエンが還流しはじめる１１０°位いよで加
熱する。しばらく加熱すると水が共沸し始めるが、これ
を連続的に分液除去し反応を１３時間継続すると水の共
沸が終了する。After dissolving, heat at about 110° where toluene begins to reflux. After heating for a while, water begins to azeotrope, but when this is continuously separated and removed and the reaction continues for 13 hours, the azeotrope of water ends.
反応液は冷却後、実施例１と同様に処理し、目的のアニ
リド２８４ｇ （収率９６％）を得た。After the reaction solution was cooled, it was treated in the same manner as in Example 1 to obtain 284 g (yield: 96%) of the desired anilide.
本発明の製造方法は、高収率で目的物が得られ、しかも
比較的短時間で反応が完結するため、工業的、経済的に
優れた製造方法である。The production method of the present invention is an industrially and economically superior production method because the desired product can be obtained in high yield and the reaction can be completed in a relatively short time.
Claims (2)
る４−クロロ− α、α、α−トリフルオロオルトトルイジンとプロポキ
シ酢酸とを置換基を有していてもよいベンゼンスルホン
酸又はナフタレンスルホン酸の存在下、脱水縮合させる
ことを特徴とする式 ▲数式、化学式、表等があります▼で表わされる４′− クロロ−２′−トリフルオロメチルプロポキシアセトア
ニリドの製造法。(1) 4-chloro- α, α, α-trifluoro-orthotoluidine and propoxyacetic acid represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ and benzenesulfonic acid or naphthalene which may have a substituent A method for producing 4'-chloro-2'-trifluoromethylpropoxyacetanilide represented by the formula ▲Mathematical formula, chemical formula, table, etc. available▼, which is characterized by dehydration condensation in the presence of sulfonic acid.
特許請求の範囲第１項記載の製造法。(2) The production method according to claim 1, in which water produced by dehydration condensation is continuously removed from the system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1080948A JPH02258752A (en) | 1989-03-31 | 1989-03-31 | Preparation of 4'-chloro-2'-trifluoromethylpropoxyacetanilide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1080948A JPH02258752A (en) | 1989-03-31 | 1989-03-31 | Preparation of 4'-chloro-2'-trifluoromethylpropoxyacetanilide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02258752A true JPH02258752A (en) | 1990-10-19 |
Family
ID=13732724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1080948A Pending JPH02258752A (en) | 1989-03-31 | 1989-03-31 | Preparation of 4'-chloro-2'-trifluoromethylpropoxyacetanilide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02258752A (en) |
-
1989
- 1989-03-31 JP JP1080948A patent/JPH02258752A/en active Pending
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