公开(公告)号：US20090287023A1

公开(公告)日：2009-11-19

申请号：US12097974

申请日：2006-12-25

申请人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

发明人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

IPC分类号： C07C209/24

CPC分类号： C07C209/62 ,  C07C209/08 ,  C07C211/21 ,  C07C211/28

摘要： Disclosed is a method for producing a primary amine compound represented by the formula (2) below, which is characterized in that a halogen compound represented by the formula (1) below, ammonia and formaldehyde are reacted with each other, and then the thus-obtained reaction product is [1] brought into contact with an aqueous solution of an acid or [2] reacted with a hydroxylamine under acidic conditions. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product. (1) (In the formula, R1 and R2 independently represent a hydrogen atom, a C1-C5 alkyl group which may be substituted by a halogen atom or the like, a C1-C5 alkoxy group which may be substituted by a halogen atom, a cyano group, a C2-C11 alkenyl group or a phenyl group or the like; R3 represents a hydrogen atom, a linear or branched C1-C5 alkyl group or a cyano group; and X represents a halogen atom.) (2) (In the formula, R1, R2 and R3 are as defined above.)

摘要翻译： 公开了下述式（2）表示的伯胺化合物的制造方法，其特征在于，将下式（1）表示的卤素化合物与氨和甲醛反应， 得到的反应产物[1]在酸性条件下与酸的水溶液或[2]与羟胺反应。 通过这种方法，可以通过使用低成本氨同时抑制作为副产物的仲胺的生产，商业上有利地生产伯胺化合物。 （1）（式中，R 1和R 2各自独立地表示氢原子，可被卤素原子等取代的C1〜C5烷基，可被卤素原子取代的C1〜C5烷氧基， 氰基，C 2 -C 11烯基或苯基等; R 3表示氢原子，直链或支链C 1 -C 5烷基或氰基; X表示卤素原子）（2）（ 在式中，R 1，R 2和R 3如上所定义。）

公开(公告)号：US07652170B2

公开(公告)日：2010-01-26

申请号：US12097974

申请日：2006-12-25

申请人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

发明人： Hiroshi Souda ,  Naoyuki Takano ,  Shinzo Seko

IPC分类号： C07C209/08

CPC分类号： C07C209/62 ,  C07C209/08 ,  C07C211/21 ,  C07C211/28

摘要： Disclosed is a method for producing a primary amine compound represented by the formula (2) below, which is characterized in that a halogen compound represented by the formula (1) below, ammonia and formaldehyde are reacted with each other, and then the thus-obtained reaction product is [1] brought into contact with an aqueous solution of an acid or [2] reacted with a hydroxylamine under acidic conditions. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product. (1) (In the formula, R1 and R2 independently represent a hydrogen atom, a C1-C5 alkyl group which may be substituted by a halogen atom or the like, a C1-C5 alkoxy group which may be substituted by a halogen atom, a cyano group, a C2-C11 alkenyl group or a phenyl group or the like; R3 represents a hydrogen atom, a linear or branched C1-C5 alkyl group or a cyano group; and X represents a halogen atom.) (2) (In the formula, R1, R2 and R3 are as defined above.)

摘要翻译： 公开了下述式（2）表示的伯胺化合物的制造方法，其特征在于，将下式（1）表示的卤素化合物与氨和甲醛反应， 得到的反应产物[1]在酸性条件下与酸的水溶液或[2]与羟胺反应。 通过这种方法，可以通过使用低成本氨同时抑制作为副产物的仲胺的生产，商业上有利地生产伯胺化合物。 （1）（式中，R 1和R 2各自独立地表示氢原子，可被卤素原子等取代的C1〜C5烷基，可被卤素原子取代的C1〜C5烷氧基， 氰基，C 2 -C 11烯基或苯基等; R 3表示氢原子，直链或支链C 1 -C 5烷基或氰基; X表示卤素原子）（2）（ 在式中，R 1，R 2和R 3如上所定义。）

公开(公告)号：US08269044B2

公开(公告)日：2012-09-18

申请号：US12097234

申请日：2006-12-14

申请人： Naoyuki Takano ,  Kazuyuki Tanaka ,  Shinzo Seko

发明人： Naoyuki Takano ,  Kazuyuki Tanaka ,  Shinzo Seko

IPC分类号： C07D213/38 ,  C07D251/04 ,  C07C209/08

CPC分类号： C07C209/62 ,  C07C213/02 ,  C07D213/26 ,  C07D213/38 ,  C07D251/04 ,  C07C211/27 ,  C07C211/29 ,  C07C217/58

摘要： Disclosed is a method for producing a primary amine compound represented by the formula (3): wherein, Ar is as defined below, which is characterized in that a halogen compound represented by the formula (1): wherein, Ar represents an unsubstituted aromatic group such as a phenyl group, a naphthyl group, a pyridyl group, a furyl group, a thienyl group, a pyrrolyl group, an oxazolyl group, an isoxazolyl group or a pyrimidinyl group, or an aromatic group obtained by substituting such an unsubstituted aromatic group with 1-3 substituents; and X represents a halogen atom, ammonia and formaldehyde are reacted with each other, thereby obtaining a hexahydrotriazine compound represented by the formula (2): wherein, Ar is as defined above, and then the thus-obtained hexahydrotriazine compound is decomposed. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product.

摘要翻译： 公开了一种由式（3）表示的伯胺化合物的制备方法：其中Ar如下所定义，其特征在于由式（1）表示的卤素化合物：其中Ar表示未取代的芳族基团 苯基，萘基，吡啶基，呋喃基，噻吩基，吡咯基，恶唑基，异恶唑基或嘧啶基，或通过取代这些未取代的芳基取代的芳基 具有1-3个取代基; X表示卤素原子，氨和甲醛彼此反应，得到式（2）表示的六氢三嗪化合物：其中，Ar如上定义，然后将由此得到的六氢三嗪化合物分解。 通过这种方法，可以通过使用低成本氨同时抑制作为副产物的仲胺的生产，商业上有利地生产伯胺化合物。

公开(公告)号：US6114543A

公开(公告)日：2000-09-05

申请号：US128974

申请日：1998-08-04

申请人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

发明人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

IPC分类号： C07D205/04

CPC分类号： C07D205/04

摘要： The present invention provides a process for preparing optically active azetidine-2-carboxylic acids using readily available reagents of relatively low price in the industry. Thus, there is provided optically active azetidine-2-carboxylic acid, and a process for producing the same by subjecting optically active N-(alkylbenzyl)azetidine-2-carboxylic acid represented by the formula (1): ##STR1## to hydrogenolysis in the presence of a catalyst.

摘要翻译： 本发明提供了使用工业中价格相对较低的容易获得的试剂制备光学活性氮杂环丁烷-2-羧酸的方法。 因此，提供光学活性的氮杂环丁烷-2-羧酸及其制备方法，其中式（1）表示的光学活性的N-（烷基苄基）氮杂环丁烷-2-羧酸：在 催化剂

公开(公告)号：US20110054185A1

公开(公告)日：2011-03-03

申请号：US11918004

申请日：2006-04-05

申请人： Kazuyuki Tanaka ,  Naoyuki Takano ,  Shinzo Seko

发明人： Kazuyuki Tanaka ,  Naoyuki Takano ,  Shinzo Seko

IPC分类号： C07D277/28

CPC分类号： C07D277/32 ,  C07D277/28 ,  C07D417/14

摘要： A process for producing a thiazole compound of the formula (3): wherein X1 is a hydrogen atom or a halogen atom, which comprises reacting a compound of the formula (1): wherein X1 is as defined above, and X2 represents a halogen atom, with ammonia and formaldehyde to obtain a hexahydrotriazine compound of the formula (2): wherein X1 is as defined above, and reacting the resulting hexahydrotriazine compound with hydroxylamine under acidic conditions. According to this process, the thiazole compound of the formula (3) can be industrially advantageously produced using inexpensive ammonia with suppressing the formation of a byproduct of the formula (4): wherein X1 is as defined above.

摘要翻译： 一种制备式（3）的噻唑化合物的方法：其中X 1是氢原子或卤素原子，其包括使式（1）的化合物：其中X 1如上所定义，X 2表示卤素原子 与氨和甲醛反应，得到式（2）的六氢三嗪化合物：其中X1如上定义，并在酸性条件下使所得六氢三嗪化合物与羟胺反应。 根据该方法，式（3）的噻唑化合物可以在工业上有利地使用廉价的氨制备，抑制式（4）的副产物的形成：其中X1如上所定义。

公开(公告)号：US07439357B2

公开(公告)日：2008-10-21

申请号：US11629754

申请日：2005-06-10

申请人： Naoyuki Takano ,  Shinzo Seko ,  Kazuyuki Tanaka

发明人： Naoyuki Takano ,  Shinzo Seko ,  Kazuyuki Tanaka

IPC分类号： C07D251/04 ,  C07D277/28

CPC分类号： C07D277/28

摘要： A process for preparing a thiazole compound of formula (3): wherein X1 represents a hydrogen atom or a halogen atom comprising reacting a compound of formula (1): wherein X1 is as defined above, and X2 represents a halogen atom, with ammonia and formaldehyde to obtain a hexahydrotriazine compound of formula (2): wherein X1 is as defined above, and hydrolyzing the compound of formula (2).

摘要翻译： 制备式（3）的噻唑化合物的方法：其中X 1表示氢原子或卤素原子，包括使式（1）化合物：其中X 1〜 >如上所定义，X 2表示卤素原子，与氨和甲醛反应，得到式（2）的六氢三嗪化合物：其中X 1如上定义 ，并水解式（2）的化合物。

公开(公告)号：US20100094022A1

公开(公告)日：2010-04-15

申请号：US12087587

申请日：2007-01-11

申请人： Naoyuki Takano ,  Morio Yamamoto ,  Shinzo Seko

发明人： Naoyuki Takano ,  Morio Yamamoto ,  Shinzo Seko

IPC分类号： C07D277/04

CPC分类号： C07D277/32

摘要： Disclosed is a simple and advantageous method for producing a thiazole compound, which method is suitable for commercial-scale implementation. In this method, a thiazole compound is produced by a reaction between 2-halogeno-allylisothiocyanate and sulfuryl chloride generating a large amount of heat, while suppressing decrease in the yield of the thiazole compound. Specifically disclosed is a method for producing 2-chloro-5-chloromethylthiazole represented by the formula (1): This method is characterized in that sulfuryl chloride is added to and reacted with 2-halogeno-allylisothiocyanate represented by the formula (2): wherein Hal represents chlorine or bromine, while blowing a gas inactive to the reaction into the reaction liquid.

摘要翻译： 本发明公开了一种生产噻唑化合物的简便有效的方法，该方法适用于商业规模的实施。 在该方法中，噻唑化合物通过2-卤代烯丙基异硫氰酸酯与磺酰氯的反应而产生，产生大量的热量，同时抑制噻唑化合物的产率降低。 具体公开的是式（1）表示的2-氯-5-氯甲基噻唑的制造方法：该方法的特征在于，向式（2）表示的2-卤代烯丙基异硫氰酸酯中加入磺酰氯，并与式 Hal代表氯或溴，同时向反应液中吹入无反应的气体。

公开(公告)号：US20090281325A1

公开(公告)日：2009-11-12

申请号：US12097234

申请日：2006-12-14

申请人： Naoyuki Takano ,  Kazuyuki Tanaka ,  Shinzo Seko

发明人： Naoyuki Takano ,  Kazuyuki Tanaka ,  Shinzo Seko

IPC分类号： C07D213/38 ,  C07C209/08

CPC分类号： C07C209/62 ,  C07C213/02 ,  C07D213/26 ,  C07D213/38 ,  C07D251/04 ,  C07C211/27 ,  C07C211/29 ,  C07C217/58

摘要： Disclosed is a method for producing a primary amine compound represented by the formula (3): wherein, Ar is as defined below , which is characterized in that a halogen compound represented by the formula (1): wherein, Ar represents an unsubstituted aromatic group such as a phenyl group, a naphthyl group, a pyridyl group, a furyl group, a thienyl group, a pyrrolyl group, an oxazolyl group, an isoxazolyl group or a pyrimidinyl group, or an aromatic group obtained by substituting such an unsubstituted aromatic group with 1-3 substituents; and X represents a halogen atom, ammonia and formaldehyde are reacted with each other, thereby obtaining a hexahydrotriazine compound represented by the formula (2): wherein, Ar is as defined above, and then the thus-obtained hexahydrotriazine compound is decomposed. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product.

摘要翻译： 公开了一种由式（3）表示的伯胺化合物的制备方法：其中Ar如下所定义，其特征在于由式（1）表示的卤素化合物：其中Ar表示未取代的芳族基团 苯基，萘基，吡啶基，呋喃基，噻吩基，吡咯基，恶唑基，异恶唑基或嘧啶基，或通过取代这些未取代的芳基取代的芳基 具有1-3个取代基; X表示卤素原子，氨和甲醛彼此反应，得到式（2）表示的六氢三嗪化合物：其中，Ar如上定义，然后将由此得到的六氢三嗪化合物分解。 通过这种方法，可以通过使用低成本氨同时抑制作为副产物的仲胺的生产，商业上有利地生产伯胺化合物。

公开(公告)号：US20070197803A1

公开(公告)日：2007-08-23

申请号：US11629754

申请日：2005-06-10

申请人： Naoyuki Takano ,  Shinzo Seko ,  Kazuyuki Tanaka

发明人： Naoyuki Takano ,  Shinzo Seko ,  Kazuyuki Tanaka

IPC分类号： C07D307/34

CPC分类号： C07D277/28

摘要： A process for preparing a thiazole compound of formula (3): wherein X1 represents a hydrogen atom or a halogen atom comprising reacting a compound of formula (1): wherein X1 is as defined above, and X2 represents a halogen atom, with ammonia and formaldehyde to obtain a hexahydrotriazine compound of formula (2): wherein X1 is as defined above, and hydrolyzing the compound of formula (2).

摘要翻译： 制备式（3）的噻唑化合物的方法：其中X 1表示氢原子或卤素原子，包括使式（1）化合物：其中X 1〜 >如上所定义，X 2表示卤素原子，与氨和甲醛反应，得到式（2）的六氢三嗪化合物：其中X 1如上定义 ，并水解式（2）的化合物。

公开(公告)号：US5880291A

公开(公告)日：1999-03-09

申请号：US924320

申请日：1997-09-05

申请人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

发明人： Hideki Ushio ,  Naoyuki Takano ,  Yukihiro Honda ,  Shinzo Seko ,  Motoo Hazama

IPC分类号： C07D205/04

CPC分类号： C07D205/04

摘要： The present invention provides a process for preparing optically active azetidine-2-carboxylic acids using readily available reagents of relatively low price in the industry. Thus, there is provided optically active azetidine-2-carboxylic acid, and a process for producing the same by subjecting optically active N-(alkylbenzyl)azetidine-2-carboxylic acid represented by the formula (1): ##STR1## to hydrogenolysis in the presence of a catalyst.

摘要翻译： 本发明提供了使用工业中价格相对较低的容易获得的试剂制备光学活性氮杂环丁烷-2-羧酸的方法。 因此，提供光学活性的氮杂环丁烷-2-羧酸及其制备方法，该方法是使式（1）表示的旋光性N-（烷基苄基）氮杂环丁烷-2-羧酸：（1） 在催化剂存在下氢解。