公开(公告)号：US20090137823A1

公开(公告)日：2009-05-28

申请号：US11989100

申请日：2006-08-01

申请人： Syuzo Satake ,  Noriyuki Hayashizaka ,  Ichiro Fuseya ,  Muneaki Tanaka ,  Hirokazu Kagano

发明人： Syuzo Satake ,  Noriyuki Hayashizaka ,  Ichiro Fuseya ,  Muneaki Tanaka ,  Hirokazu Kagano

IPC分类号： C07D333/22

CPC分类号： C07D333/22

摘要： The present invention provides a process for producing (E)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine represented by Formula (1); wherein R is a C1-4 alkyl, the method comprising the steps of: maintaining a solution containing (Z)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine dissolved therein at 25° C. or below to deposit crystals and separating crystals having a particle diameter of 100 μm or less from the deposited crystals; and a process for producing (E,Z)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine comprising the steps of: reacting an alkali metal salt of β-oxo-β-(2-thienyl)propanal with a monoalkylamine compound; adding a water-insoluble organic solvent to the resulting reaction mixture; adding seed crystals containing (E)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine to an organic layer obtained by conducting separation; and keeping the resulting mixture at 25° C. or below.

摘要翻译： 本发明提供由式（1）表示的（E）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的制备方法。 其中R是C 1-4烷基，所述方法包括以下步骤：在25℃以下溶解含有（Z）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的溶液， 从沉积的晶体中沉积晶体并分离出粒径为100μm以下的晶体; 和（E，Z）-N-单烷基-3-氧代-3-（2-噻吩基）丙胺的制备方法，包括以下步骤：使β-氧代-β-（2-噻吩基）丙醛的碱金属盐 与单烷基胺化合物; 向所得反应混合物中加入水不溶性有机溶剂; 将含有（E）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的晶种加入到通过分离获得的有机层中; 并将所得混合物保持在25℃或更低。

公开(公告)号：US07829730B2

公开(公告)日：2010-11-09

申请号：US12297276

申请日：2007-04-04

申请人： Takehiro Hiyama ,  Takeshi Takeuchi ,  Hidehiko Myoken ,  Hirokazu Kagano

发明人： Takehiro Hiyama ,  Takeshi Takeuchi ,  Hidehiko Myoken ,  Hirokazu Kagano

IPC分类号： C07D549/11 ,  C07D341/00

CPC分类号： C07D327/00

摘要： The present invention provides a process for producing a methylene disulfonate compound in a simple manner at low cost.The present invention provides a process for producing a methylene disulfonate compound represented by General Formula (2) comprising: reacting, in the presence of a dehydrating agent, a formaldehyde compound with a sulfonic acid compound represented by General Formula (1): wherein R1 and R2 are independently a hydrogen atom or a C1-4 alkyl group whose hydrogen atom may be substituted with halogen atom; n is an integer from 1 to 4; and when n is an integer from 2 to 4, n R1s and n R2s may be the same or different: wherein, R1, R2, and n are the same as those described above for General Formula (1).

摘要翻译： 本发明以简单的方式提供以低成本生产亚甲基二磺酸酯化合物的方法。 本发明提供一种制备由通式（2）表示的亚甲基二磺酸盐化合物的方法，包括：在脱水剂存在下使甲醛化合物与通式（1）表示的磺酸化合物反应：其中R1和 R2独立地为氢原子或氢原子可被卤素原子取代的C1-4烷基; n是1至4的整数; 当n为2〜4的整数时，n R 1和n R 2可以相同或不同：其中，R 1，R 2和n与上述通式（1）相同。

公开(公告)号：US07759501B2

公开(公告)日：2010-07-20

申请号：US10523287

申请日：2003-07-15

申请人： Kenji Kogami ,  Noriyuki Hayashizaka ,  Syuzo Satake ,  Ichiro Fuseya ,  Hirokazu Kagano

发明人： Kenji Kogami ,  Noriyuki Hayashizaka ,  Syuzo Satake ,  Ichiro Fuseya ,  Hirokazu Kagano

IPC分类号： C07D333/20 ,  C07D333/22

CPC分类号： C07D333/22 ,  C07D333/20

摘要： The present invention provides a process for producing an N-monoalkyl-3-hydroxy-3-(2-thienyl)propanamine represented by General Formula (2): wherein R is C1-4 alkyl, comprising the step of reducing (Z)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine represented by General Formula (1): wherein R is as defined above. According to the present invention, an N-monoalkyl-3-hydroxy-3-(2-thienyl)propanamine which is for use as an intermediate for various pharmaceuticals can be produced in an industrially inexpensive and easy manner.

摘要翻译： 本发明提供了制备由通式（2）表示的N-单烷基-3-羟基-3-（2-噻吩基）丙胺的方法：其中R是C 1-4烷基，包括还原（Z） - 由通式（1）表示的N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺：其中R如上所定义。 根据本发明，用作各种药物的中间体的N-单烷基-3-羟基-3-（2-噻吩基）丙胺可以以工业上便宜且容易的方式制备。

公开(公告)号：US20120149917A1

公开(公告)日：2012-06-14

申请号：US13396972

申请日：2012-02-15

申请人： Syuzo SATAKE ,  Noriyuki Hayashizaka ,  Ichiro Fuseya ,  Muneaki Tanaka ,  Hirokazu Kagano

发明人： Syuzo SATAKE ,  Noriyuki Hayashizaka ,  Ichiro Fuseya ,  Muneaki Tanaka ,  Hirokazu Kagano

IPC分类号： C07D333/22

CPC分类号： C07D333/22

摘要： The present invention provides a process for producing (E)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine represented by Formula (1); wherein R is a C1-4 alkyl, the method comprising the steps of: maintaining a solution containing (Z)—N-monoalkyl-3-oxo-3-(2-thienyl)propenamine dissolved therein at 25° C. or below to deposit crystals and separating crystals having a particle diameter of 100 μm or less from the deposited crystals; and a process for producing (E,Z)—N-monoalkyl-3-oxo-3-(2-thienyl)propenamine comprising the steps of: reacting an alkali metal salt of β-oxo-β-(2-thienyl)propanal with a monoalkylamine compound; adding a water-insoluble organic solvent to the resulting reaction mixture; adding seed crystals containing (E)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine to an organic layer obtained by conducting separation; and keeping the resulting mixture at 25° C. or below.

摘要翻译： 本发明提供由式（1）表示的（E）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的制备方法。 其中R是C 1-4烷基，所述方法包括以下步骤：在25℃以下溶解含有（Z）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的溶液， 从沉积的晶体沉积晶体并分离出粒径为100μm以下的晶体; 和（E，Z）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的制备方法，包括以下步骤：使＆bgr-氧代 - （2-噻吩基） ）丙醛与单烷基胺化合物; 向所得反应混合物中加入水不溶性有机溶剂; 将含有（E）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的晶种加入到通过分离获得的有机层中; 并将所得混合物保持在25℃或更低。

公开(公告)号：US5773626A

公开(公告)日：1998-06-30

申请号：US718132

申请日：1996-09-18

申请人： Hirokazu Kagano ,  Hiroshi Goda ,  Katsuhiko Yoshida ,  Mikio Yamamoto ,  Shigeki Sakaue

发明人： Hirokazu Kagano ,  Hiroshi Goda ,  Katsuhiko Yoshida ,  Mikio Yamamoto ,  Shigeki Sakaue

IPC分类号： C07D275/04 ,  C07D275/06

CPC分类号： C07D275/04 ,  C07D275/06

摘要： A method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-(alkylthio)benzaldehyde with a hydroxylamine to give a 2-(alkylthio)benzaldehyde oxime and carrying out a reaction of the 2-(alkylthio)benzaldehyde oxime with a halogenating agent; and a method for producing a 1,2-benzisothiazol-3-one, having the steps of carrying out a reaction of a 2-halobenzonitrile with an alkanethiol in a heterogeneous solvent system in the presence of a base to give a 2-(alkylthio)benzonitrile and carrying out a reaction of the 2-(alkylthio)benzonitrile with an halogenating agent in the presence of water.

摘要翻译： 一种1,2-苯并异噻唑-3-酮的制备方法，其具有2-（烷硫基）苯甲醛与羟胺反应的步骤，得到2-（烷硫基）苯甲醛肟，进行 2-（烷硫基）苯甲醛肟与卤化剂; 和1,2-苯并异噻唑-3-酮的制备方法，其具有以下步骤：在非均相溶剂体系中，在碱的存在下，使2-卤代苄腈与链烷硫醇进行反应，得到2-（烷硫基 ）苄腈，并在水存在下进行2-（烷硫基）苄腈与卤化剂的反应。

公开(公告)号：US5508416A

公开(公告)日：1996-04-16

申请号：US342038

申请日：1994-11-17

申请人： Hirokazu Kagano ,  Hiroshi Goda ,  Shigeki Sakaue

发明人： Hirokazu Kagano ,  Hiroshi Goda ,  Shigeki Sakaue

IPC分类号： C07C315/02 ,  C07C317/44 ,  C07C319/14 ,  C07C319/18 ,  C07C323/62 ,  C07D275/04

CPC分类号： C07D275/04 ,  C07C315/02 ,  C07C319/14 ,  C07C319/18 ,  C07C2101/14

摘要： A method for producing an alkylthiobenzamide by carrying out a reaction of a halobenzamide with an alkanethiol in the presence of a base in a heterogeneous solvent; a method for producing an alkylsulfinylbenzamide by carrying out a reaction of an alkylthiobenzamide with a halogen in a heterogeneous solvent; a method for producing an alkylsulfinylbenzamide by carrying out a reaction of a halobenzamide with an alkanethiol in the presence of a base in a heterogeneous solvent and a subsequent reaction with a halogen; and a method for producing a 1,2-benzisothiazol-3-one by carrying out a reaction of a 2-(alkylthio)benzamide with a halogenating agent.

摘要翻译： 一种烷基硫代苯甲酰胺的制备方法，其通过在非均相溶剂中在碱存在下进行卤代苯甲酰胺与烷硫醇的反应; 通过在异质溶剂中进行烷基硫代苯甲酰胺与卤素的反应制备烷基亚磺酰基苯甲酰胺的方法; 烷基亚磺酰基苯甲酰胺的制备方法，其通过在碱存在下在非均相溶剂中进行卤代苯甲酰胺与烷硫醇的反应，随后与卤素反应; 和通过2-（烷硫基）苯甲酰胺与卤化剂的反应制备1,2-苯并异噻唑-3-酮的方法。

公开(公告)号：US5298630A

公开(公告)日：1994-03-29

申请号：US945084

申请日：1992-09-15

申请人： Hirokazu Kagano ,  Hiroshi Goda ,  Katsuhiko Yoshida ,  Masahito Nakano

发明人： Hirokazu Kagano ,  Hiroshi Goda ,  Katsuhiko Yoshida ,  Masahito Nakano

IPC分类号： C07C319/14 ,  C07C323/22 ,  C07D333/56 ,  C07D333/70

CPC分类号： C07D333/70 ,  C07C319/14 ,  C07D333/56

摘要： A 2-alkylthiobenzaldehyde of general formula (I) is reacted with a halo compound of general formula (II) to produce a 2-substituted benzo[b]thiophene of general formula (III): ##STR1## wherein R.sup.1 means an alkyl group of 1 to 4 carbon atoms,X.sup.1 CH.sub.2 Y (II)wherein X.sup.1 means Cl or Br; Y means --CO.sub.2 H, --CO.sub.2 R.sup.2, --COR.sup.2, --CONH.sub.2 or --CN; R.sup.2 means an alkyl group of 1 to 4 carbon atoms, ##STR2## wherein Y is as defined above. The process of this invention is of great economic and industrial value, for 2-acetylbenzo[b]thiophene and 2-benzo[b]thiophenecarboxylic acid, which are important intermediates for drugs and agricultural chemicals among others, can be obtained in a simple manner, easily and in high yield.

摘要翻译： 将通式（I）的2-烷硫基苯甲醛与通式（II）的卤代化合物反应，生成通式（III）的2-取代苯并（b）噻吩：（*化学结构*）（I）其中 R1表示1〜4个碳原子的烷基，X1CH2Y（Ⅱ）其中X1表示Cl或Br; Y表示-CO 2 H，-CO 2 R 2，-COR 2，-CONH 2或-CN; R2表示1〜4个碳原子的烷基，（*化学结构*）（III）其中Y如上定义。 本发明的方法具有很大的经济和工业价值，可以以简单的方式获得作为药物和农药等重要中间体的2-乙酰基苯并（b）噻吩和2-苯并（b）噻吩羧酸 ，容易和高产量。

公开(公告)号：US5210291A

公开(公告)日：1993-05-11

申请号：US794906

申请日：1991-11-20

申请人： Michio Suzuki ,  Hiroyuki Hata ,  Masato Yoshikawa ,  Toshiyuki Ohe ,  Hirokazu Kagano ,  Hiroshi Goda ,  Masahito Nakano ,  Masaki Teramoto

发明人： Michio Suzuki ,  Hiroyuki Hata ,  Masato Yoshikawa ,  Toshiyuki Ohe ,  Hirokazu Kagano ,  Hiroshi Goda ,  Masahito Nakano ,  Masaki Teramoto

IPC分类号： C07C319/14 ,  C07C323/52

CPC分类号： C07C319/14 ,  C07C323/52

摘要： The present invention is directed to a method for producing dichlorophenylthioglycolic acid which comprises reacting monobromodichlorobenzene or trichlorobenzene with a thioglycolate in a ratio of 0.5 to 2.5 mols of the latter to 1 mol of the former in a polar solvent, and to a method for producing dichlorophenylthioglycolic acid comprising further reacting the reaction mixture obtained as above with a monohalogenoacetate.The method of the present invention is very useful industrially, advantageously producing dichlorophenylthioglycolic acid in high yield.

公开(公告)号：US08183392B2

公开(公告)日：2012-05-22

申请号：US11989100

申请日：2006-08-01

申请人： Syuzo Satake ,  Noriyuki Hayashizaka ,  Ichiro Fuseya ,  Muneaki Tanaka ,  Hirokazu Kagano

发明人： Syuzo Satake ,  Noriyuki Hayashizaka ,  Ichiro Fuseya ,  Muneaki Tanaka ,  Hirokazu Kagano

IPC分类号： C07D333/22

CPC分类号： C07D333/22

摘要： The present invention provides a process for producing (E)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine represented by Formula (1); wherein R is a C1-4 alkyl, the method comprising the steps of: maintaining a solution containing (Z)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine dissolved therein at 25° C. or below to deposit crystals and separating crystals having a particle diameter of 100 μm or less from the deposited crystals; and a process for producing (E,Z)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine comprising the steps of: reacting an alkali metal salt of β-oxo-β-(2-thienyl)propanal with a monoalkylamine compound; adding a water-insoluble organic solvent to the resulting reaction mixture; adding seed crystals containing (E)-N-monoalkyl-3-oxo-3-(2-thienyl)propenamine to an organic layer obtained by conducting separation; and keeping the resulting mixture at 25° C. or below.

摘要翻译： 本发明提供由式（1）表示的（E）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的制备方法。 其中R是C 1-4烷基，所述方法包括以下步骤：在25℃以下溶解含有（Z）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的溶液， 从沉积的晶体沉积晶体并分离出粒径为100μm以下的晶体; 和（E，Z）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的制备方法，包括以下步骤：使＆bgr-氧代 - （2-噻吩基） ）丙醛与单烷基胺化合物; 向所得反应混合物中加入水不溶性有机溶剂; 将含有（E）-N-单烷基-3-氧代-3-（2-噻吩基）丙烯胺的晶种加入到通过分离获得的有机层中; 并将所得混合物保持在25℃或更低。

公开(公告)号：US07659411B2

公开(公告)日：2010-02-09

申请号：US10579734

申请日：2004-12-13

申请人： Seiji Bando ,  Syuzo Satake ,  Hirokazu Kagano

发明人： Seiji Bando ,  Syuzo Satake ,  Hirokazu Kagano

IPC分类号： C07D333/28 ,  C07D333/22 ,  A61K31/38 ,  A01N43/06

CPC分类号： C07D333/22

摘要： The present invention provides a process for producing a 2-acylthiophene compound which has a low content of the 3-isomer generated as a by-product, the process comprising reacting a thiophene compound represented by formula (1): wherein R1is a hydrogen atom, a C1-6 alkyl group, a phenyl group, or a halogen atom, with at least one member selected from the group consisting of acid anhydrides represented by formula (2): wherein R2 is a C1-6 alkyl group or a phenyl group, and acid halides represented by formula (3): wherein R2 is as defined above and X is a halogen atom, in the presence of a solid acid catalyst at a temperature less than 75° C. in the absence of solvent, thus producing a 2-acylthiophene compound represented by formula (4): wherein R1 and R2 are as defined above.

摘要翻译： 本发明提供一种生产副产物3-异构体含量低的2-酰基噻吩化合物的方法，该方法包括使由式（1）表示的噻吩化合物：其中R 1为氢原子， C 1-6烷基，苯基或卤素原子，与选自由式（2）表示的酸酐中的至少一种：其中R2是C1-6烷基或苯基， 和式（3）表示的酰基卤：其中R 2如上所定义，X为卤素原子，在不存在溶剂的情况下，在固体酸催化剂存在下，在低于75℃的温度下，产生2 （4）表示的α-酰基噻吩化合物：其中R1和R2如上定义。