JPS6253509B2 - - Google Patents
Info
- Publication number
- JPS6253509B2 JPS6253509B2 JP1019381A JP1019381A JPS6253509B2 JP S6253509 B2 JPS6253509 B2 JP S6253509B2 JP 1019381 A JP1019381 A JP 1019381A JP 1019381 A JP1019381 A JP 1019381A JP S6253509 B2 JPS6253509 B2 JP S6253509B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alcohol
- water
- product
- acetoacetanilides
- 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.)
- Expired
Links
- 238000006243 chemical reaction Methods 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 10
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 9
- -1 aromatic primary amine Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000002635 aromatic organic solvent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- HBSBCQFSNGJXQX-UHFFFAOYSA-N 4-chloro-n-(2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(OC)C(NC(=O)CC(=O)CCl)=C1 HBSBCQFSNGJXQX-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 1
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 1
- MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は、アゾ顔料の中間体として有用なアセ
トアセトアニリド類の製造法に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing acetoacetanilides useful as intermediates for azo pigments.
従来のアセトアセトアニリド類の製造法は、芳
香族第一アミンとジケテンとを、例えばジヨン・
ウイリイ・アンドサンズ発行、オーガニツク・シ
ンセシス第３巻に記載されている如く、ベンゼ
ン、トルエン、キシレン等のジケテンに対して不
活性な芳香族有機溶媒中で反応させる方法、米国
特許第3304328号、特公昭33−2278号、特開昭51
−131840号明細書等に開示されている如く、水溶
媒中で反応させる方法及び特開昭51−131836号明
細書に開示されている如く、酢酸水溶液中で反応
させる方法とに大別される。 The conventional method for producing acetoacetanilides is to combine an aromatic primary amine and a diketene with, for example, dione,
As described in Organic Synthesis, Vol. 3, published by Willy & Sons, there is a method of reacting diketenes in an inert aromatic organic solvent such as benzene, toluene, and xylene, US Pat. No. 3,304,328, esp. Publication No. 33-2278, Japanese Unexamined Patent Publication No. 1973
It can be roughly divided into a method of reacting in an aqueous solvent as disclosed in JP-A-131840, etc., and a method of reacting in an aqueous acetic acid solution as disclosed in JP-A-51-131836. .
しかしながら、不活性芳香族有機溶媒法では、
高純度のアセトアセトアニリド類を製造し易い反
面、収率が低いという欠点を有し、また、水溶媒
法では、収率が高い反面、反応系をできるだけ均
一にし、且つ生成物の凝固を防ぐために、特殊な
高速撹拌装置や界面活性剤の添加を必要とする
し、特に原料として水不溶性固体アミンを使用す
る場合には生成物中に当該未反応アミンが混入し
易く、界面活性剤と共に顔料特性に悪影響を及ぼ
す難点がある。更に、酢酸法では、特に腐蝕の問
題から、反応設備等の材質の選定に制約があるこ
とや、酢酸回収面での難点がある。 However, in the inert aromatic organic solvent method,
Although it is easy to produce high-purity acetoacetanilides, it has the disadvantage of low yields.Also, while the aqueous solvent method has high yields, it is necessary to make the reaction system as homogeneous as possible and prevent the product from coagulating. , special high-speed stirring equipment and the addition of a surfactant are required, and especially when a water-insoluble solid amine is used as a raw material, the unreacted amine is likely to be mixed into the product, and together with the surfactant, the pigment properties may be affected. There are drawbacks that can have a negative impact on Furthermore, in the acetic acid method, there are restrictions in the selection of materials for reaction equipment, etc., particularly due to corrosion problems, and there are difficulties in recovering acetic acid.
本発明者等は、かかる従来法の欠点を解消する
ため鋭意研究を重ねた結果、
一般式
（式中、Ｘは塩素原子、Ｙは低級アルキル基、Ｚ
は低級アルコキシ基を表わし、ｌは０又は１、ｍ
及びｎはそれぞれ０、１又は２を表わす）
で示される芳香族第一アミンとジケテンとを反応
させてアセトアセトアニリド類を製造する際、当
該反応を水溶性アルコール又はその水溶液中で行
なわせると共に、生成物たるアセトアセトアニリ
ド類を当該アルコール又はその水溶液に溶解させ
た後、反応液を水で希釈し生成物を析出させるこ
とにより、低廉な設備で高純度、高収率にてアセ
トアセトアニリド類を製造し得ることを見い出
し、本発明を完成するに至つた。 As a result of intensive research to eliminate the drawbacks of such conventional methods, the present inventors found that the general formula (In the formula, X is a chlorine atom, Y is a lower alkyl group, Z
represents a lower alkoxy group, l is 0 or 1, m
and n each represent 0, 1 or 2) When producing acetoacetanilides by reacting an aromatic primary amine represented by the following with diketene, the reaction is carried out in a water-soluble alcohol or an aqueous solution thereof, and After dissolving the product acetoacetanilide in the alcohol or its aqueous solution, the reaction solution is diluted with water and the product is precipitated to produce acetoacetanilide with high purity and high yield using inexpensive equipment. They have discovered that it is possible to do so, and have completed the present invention.
本発明では、通常、一般式（）で示される芳
香族第一アミンを水溶性アルコール又は当該アル
コールの50重量％（以下特に記載のない限り％は
重量％を表わす）以上好ましくは80％以上の濃度
の水溶液に懸濁又は溶解させた後、無触媒下又は
酢酸、硫酸、塩酸、リン酸等の酸類を触媒として
用い、20〜60℃の温度範囲で、当該アミンに対し
て当量又は５モル％以下の小過剰量のジケテンと
反応させると共に、生成したアセトアセトアニリ
ド類を当該アルコール又はその水溶液に溶解させ
る。アルコール水溶液の濃度、量、反応温度等
は、当該アルコール及び芳香族第一アミンの種類
にもよるが、反応終了後の反応系中にアセトアセ
トアニリド類が溶解している様適宜選択すれば良
い。反応終了後、アセトアセトアニリド類が溶解
されている反応系を水で希釈しアセトアセトアニ
リド類を析出させる際、加える水の量は、当該反
応系におけるアルコール水溶液のアルコール濃度
が通常20〜70％、好ましくは40〜60％となる様に
用いればよい。次いで、析出した結晶を取し、
水で洗浄することにより、純度99％以上のアセト
アセトアニリド類が95％以上の高収率で得られ、
このまゝアゾ顔料の中間体として使用することが
できる。また別したアルコール水溶液を蒸留し
アルコールを回収すれば次の反応溶媒として再使
用することができる。 In the present invention, the aromatic primary amine represented by the general formula () is usually used in a water-soluble alcohol or in an amount of 50% by weight (hereinafter, unless otherwise specified, % represents weight%) or more, preferably 80% or more of the alcohol. After suspending or dissolving it in an aqueous solution with a concentration of % or less of diketene, and the produced acetoacetanilides are dissolved in the alcohol or its aqueous solution. The concentration, amount, reaction temperature, etc. of the aqueous alcohol solution may be appropriately selected so that the acetoacetanilide is dissolved in the reaction system after the reaction, although it depends on the type of alcohol and aromatic primary amine. After completion of the reaction, when diluting the reaction system in which the acetoacetanilides are dissolved with water to precipitate the acetoacetanilides, the amount of water added is such that the alcohol concentration of the aqueous alcohol solution in the reaction system is usually 20 to 70%, preferably may be used so that it becomes 40 to 60%. Next, take the precipitated crystals,
By washing with water, acetoacetanilides with a purity of 99% or higher can be obtained in a high yield of 95% or higher.
It can be used as an intermediate for azo pigments. Furthermore, if the alcohol is recovered by distilling the separate aqueous alcohol solution, it can be reused as the next reaction solvent.
本発明において用いられる一般式（）で示さ
れる芳香族第一アミンとしては、例えばアニリ
ン、ｏ−クロロアニリン、ｍ−クロロアニリン、
ｏ−トルイジン、ｐ−トルイジン、ｍ−キシリジ
ン、ｏ−アニシジン、ｐ−アニシジン、２・４−
ジメトキシアニリン、２・５−ジメトキシアニリ
ン、４−クロロ−２・５−ジメトキシアニリン、
０−エトキシアニリン、ｐ−エトキシアニリン等
が挙げられる。また水溶性アルコールとしては、
メタノール、エタノール、イソプロピルアルコー
ル、ｎ−プロピルアルコール等が挙げられるが、
経済的にはメタノールが好ましい。 Examples of the aromatic primary amine represented by the general formula () used in the present invention include aniline, o-chloroaniline, m-chloroaniline,
o-toluidine, p-toluidine, m-xylidine, o-anisidine, p-anisidine, 2.4-
Dimethoxyaniline, 2,5-dimethoxyaniline, 4-chloro-2,5-dimethoxyaniline,
Examples include 0-ethoxyaniline and p-ethoxyaniline. In addition, as water-soluble alcohol,
Examples include methanol, ethanol, isopropyl alcohol, n-propyl alcohol, etc.
Economically, methanol is preferred.
尚、アルコール類は、一般にジケテンと反応し
てアセトアセチルエステルを生成するが、本発明
に係る反応では、ジケテンが殆んど選択的に芳香
族第一アミンと反応するため、アルコールとの副
反応はほとんど無視し得る。 Incidentally, alcohols generally react with diketene to produce acetoacetyl ester, but in the reaction according to the present invention, diketene reacts almost selectively with aromatic primary amines, so there is no side reaction with alcohol. can be almost ignored.
次に実施例により本発明を説明する。 Next, the present invention will be explained with reference to Examples.
実施例 １
滴下漏斗、リフラツクスコンデンサー及び温度
計を付けた１の四つ口フラスコの中で、４−ク
ロロ−２・５−ジメトキシアニリン187.5ｇ
（1mol）を濃度99％のメタノール300ｇに懸濁さ
せた後、撹拌しながら50℃に昇温した。この温度
でジケテン88.2ｇ（1.05mol）を滴下し、更に１
時間同温度で反応させて、生成物を反応液中に溶
解させた。この反応液中にメタノール水溶液中の
メタノール濃度が50％となる様50℃の温水300ｇ
を滴下すると、結晶が析出した。反応液を20℃ま
で冷却し当該結晶をヌツチエにて吸引過した
後、50％メタノール水溶液100ｇで洗浄し更に水
100ｇで洗浄して乾燥すると、融点105〜106℃の
4′−クロロ−2′・5′−ジメトキシアセトアセトア
ニリドの白色結晶261ｇ（収率96％）が得られ
た。Example 1 In a four-neck flask equipped with a dropping funnel, reflux condenser, and thermometer, 187.5 g of 4-chloro-2,5-dimethoxyaniline.
(1 mol) was suspended in 300 g of methanol with a concentration of 99%, and the temperature was raised to 50° C. with stirring. At this temperature, 88.2 g (1.05 mol) of diketene was added dropwise, and 1.
The reaction was carried out for the same time and temperature to dissolve the product in the reaction solution. Add 300 g of warm water at 50℃ to this reaction solution so that the methanol concentration in the methanol aqueous solution is 50%.
When added dropwise, crystals precipitated. The reaction solution was cooled to 20°C and the crystals were filtered by suction using a Nutsuchie filter, washed with 100 g of a 50% methanol aqueous solution, and further washed with water.
When washed and dried with 100g, it has a melting point of 105-106℃.
261 g (yield: 96%) of white crystals of 4'-chloro-2',5'-dimethoxyacetoacetanilide were obtained.
実施例 ２
実施例１におけるメタノール溶媒の代りに濃度
80％のメタノール水溶液を用い、実施例１におけ
る場合と同じ条件下で反応させて、生成物を反応
液中に溶解させた後、結晶を析出させて取する
と、融点105〜106℃の4′−クロロ−2′・5′−ジメ
トキシアセトアセトアニリドの白色結晶261ｇ
（収率96％）が得られた。Example 2 Concentration instead of methanol solvent in Example 1
Using an 80% methanol aqueous solution, the reaction was carried out under the same conditions as in Example 1, and after the product was dissolved in the reaction solution, crystals were precipitated and collected. -261g of white crystals of chloro-2',5'-dimethoxyacetoacetanilide
(yield 96%) was obtained.
実施例 ３
実施例１における場合と同じ装置を用い、ｍ−
キシリジン121ｇ（1mol）を濃度99％のメタノー
ル300ｇに溶解させ、撹拌しながら50℃にてジケ
テン88.2ｇ（1.05mol）を滴下反応させて、生成
物を反応液中に溶解させた後、実施例１における
場合と同様に処理すると、融点89.0〜90.0℃の
2′・4′−ジメチルアセトアセトアニリドの白色結
晶195ｇ（収率95％）が得られた。Example 3 Using the same equipment as in Example 1, m-
121 g (1 mol) of xylidine was dissolved in 300 g of methanol with a concentration of 99%, and 88.2 g (1.05 mol) of diketene was added dropwise to react at 50°C with stirring. After dissolving the product in the reaction solution, Example When treated in the same manner as in 1, a product with a melting point of 89.0-90.0℃
195 g (yield: 95%) of white crystals of 2',4'-dimethylacetoacetanilide were obtained.
実施例 ４
実施例１における場合と同じ装置を用い０−ク
ロルアニリン127.5ｇ（1mol）を濃度99％のメタ
ノール300ｇに溶解させ、触媒として氷酢酸0.6ｇ
（0.01mol）を添加後、撹拌しながら50℃にてジケ
テン88.2ｇ（1.05mol）を滴下反応させて、生成
物を反応液中に溶解させた後、実施例１における
場合と同様に処理すると、融点104.0〜105.0℃の
2′−クロロアセトアセトアニリドの白色結晶201
ｇ（収率95％）が得られた。Example 4 Using the same apparatus as in Example 1, 127.5 g (1 mol) of 0-chloroaniline was dissolved in 300 g of methanol with a concentration of 99%, and 0.6 g of glacial acetic acid was used as a catalyst.
After adding (0.01 mol), 88.2 g (1.05 mol) of diketene was added dropwise at 50°C with stirring to dissolve the product in the reaction solution, and then treated in the same manner as in Example 1. , melting point 104.0~105.0℃
White crystals of 2′-chloroacetoacetanilide 201
g (yield 95%) was obtained.
実施例 ５
実施例１におけるメタノール溶媒の代りに、濃
度99％のイソプロピルアルコールを用い、実施例
１における場合と同じ条件下で反応させて、生成
物を反応液中に溶解させた後、イソプロピルアル
コール水溶液中のイソプロピルアルコール濃度が
40％となる様50℃の湯水を滴下すると結晶が析出
した。反応液を実施例１における場合と同様に処
理すると、融点105〜106℃の4′−クロロ−2′・
5′−ジメトキシアセトアセトアニリドの白色結晶
258ｇ（収率95％）が得られた。Example 5 Using isopropyl alcohol with a concentration of 99% in place of the methanol solvent in Example 1, the reaction was carried out under the same conditions as in Example 1, and after dissolving the product in the reaction solution, isopropyl alcohol was used. Isopropyl alcohol concentration in aqueous solution
When hot water at 50°C was added dropwise to give a concentration of 40%, crystals precipitated. When the reaction solution was treated in the same manner as in Example 1, 4'-chloro-2'.
White crystals of 5'-dimethoxyacetoacetanilide
258g (95% yield) was obtained.
Claims (1)
は低級アルコキシ基を表わし、ｌは０又は１、ｍ
及びｎはそれぞれ０、１又は２を表わす） で示される芳香族第一アミンとジケテンとを反応
させてアセトアセトアニリド類を製造する際、当
該反応を水溶性アルコール又はその水溶液中で行
なわせると共に、生成物たるアセトアセトアニリ
ド類を当該アルコール又はその水溶液に溶解させ
た後、反応液を水で希釈し生成物を析出させるこ
とを特徴とするアセトアセトアニリド類の製造
法。[Claims] 1. General formula (In the formula, X is a chlorine atom, Y is a lower alkyl group, Z
represents a lower alkoxy group, l is 0 or 1, m
and n each represent 0, 1 or 2) When producing acetoacetanilides by reacting an aromatic primary amine represented by the following with diketene, the reaction is carried out in a water-soluble alcohol or an aqueous solution thereof, and 1. A method for producing acetoacetanilides, which comprises dissolving the acetoacetanilide product in the alcohol or its aqueous solution, and then diluting the reaction solution with water to precipitate the product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1019381A JPS57126453A (en) | 1981-01-28 | 1981-01-28 | Production of acetoacetic anilide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1019381A JPS57126453A (en) | 1981-01-28 | 1981-01-28 | Production of acetoacetic anilide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57126453A JPS57126453A (en) | 1982-08-06 |
| JPS6253509B2 true JPS6253509B2 (en) | 1987-11-10 |
Family
ID=11743446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1019381A Granted JPS57126453A (en) | 1981-01-28 | 1981-01-28 | Production of acetoacetic anilide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57126453A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104292121A (en) * | 2014-09-05 | 2015-01-21 | 南通醋酸化工股份有限公司 | Method for reducing byproducts in o-methyl-N-acetoacetanilide production |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6036249A (en) * | 1983-08-08 | 1985-02-25 | Fuji Syst Kiki Kk | Device for monitoring movement of thin sheet |
| DE4335614A1 (en) * | 1993-10-19 | 1995-04-27 | Hoechst Ag | Process for the preparation of 5-acetoacetylaminobenzimidazolone-2 |
| DE4335613A1 (en) * | 1993-10-19 | 1995-04-20 | Hoechst Ag | Process for the preparation of acetoacetarylamides |
| EP1712544A1 (en) * | 2005-04-12 | 2006-10-18 | Lonza Ag | Process for the Preparation of N-Arylamides of Acetoacetic Acid |
| CN104119247B (en) * | 2014-08-05 | 2017-04-05 | 响水恒利达科技化工有限公司 | A kind of preparation method of 4 chlorine, 2,5 dimethoxy AAA |
| CN106588685B (en) * | 2016-12-14 | 2019-03-01 | 南通醋酸化工股份有限公司 | 2,5- of one kind dimethoxy-4 '-chloracetyl antifebrin preparation method |
-
1981
- 1981-01-28 JP JP1019381A patent/JPS57126453A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104292121A (en) * | 2014-09-05 | 2015-01-21 | 南通醋酸化工股份有限公司 | Method for reducing byproducts in o-methyl-N-acetoacetanilide production |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57126453A (en) | 1982-08-06 |
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