公开(公告)号：EP0952143A1

公开(公告)日：1999-10-27

申请号：EP99302699.6

申请日：1999-04-07

Applicant: ROHM AND HAAS COMPANY

Inventor： Rayle, Heather Lynnette

IPC: C07C231/10 ,  C07D263/32 ,  C07C233/31 ,  C07C233/32 ,  C07C233/76

CPC classification number: C07C231/12 ,  C07C231/10 ,  C07C231/14 ,  C07D263/32 ,  C07C233/31 ,  C07C233/76

Abstract: This invention relates to a process for the preparation of an α-chloroketone compound comprising the steps of

(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline

(ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate
and
(iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone
wherein

Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,
R is a hydrogen atom or alkyl, and
R 1 and R 2 are each independently an alkyl or substituted alkyl group, or R 1 and R 2 together with the carbon atom to which they are attached form a cyclic structure.


Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.

Abstract translation: 本发明涉及一种用于一个alpha氯酮化合物包含式（I）中的步骤环化，以炔基酰胺制备，以形成5-亚甲基恶唑的制备（ⅱ）使用氯化三氯异氰尿酸生成氯化5-亚甲基恶唑啉 恶唑啉中间体和（iii）水解氯代恶唑啉与wässrige酸，以产生所需的一氯代氢中间 worin Z是烷基或substituiertem烷基，芳基或substituiertem芳基，杂芳基或substituiertem杂芳基或亚苯基，R是一个 原子或烷基，且R <1>和R <2>是烷基或substituiertem烷基的每个unabhängig，或R <1>和R <2>与碳原子一起与它们所连接形成环状结构。 此外，当R为氢原子，一氯代酮可以方便地通过反应条件的调整而形成。

公开(公告)号：EP0872473A3

公开(公告)日：2002-01-02

申请号：EP98302710.3

申请日：1998-04-07

Applicant: ROHM AND HAAS COMPANY

Inventor： Rayle, Heather Lynnette ,  Roemmele, Renee Caroline ,  Stephens, Randall Wayne ,  Chong, Joshua Anthony ,  Abdesaken, Fereydon ,  Wu, Charles Chao

IPC: C07C221/00 ,  C07C225/06 ,  C07C225/10 ,  C07D263/38

CPC classification number: C07C221/00 ,  C07C225/06 ,  C07C225/10

Abstract: The present invention relates to a process for preparing 5-methylene cyclic carbamates either by cyclization of an alkynyl amine with carbon dioxide in the presence of a copper catalyst or by forming an isocyanate from a substituted acetoacetamide followed by hydrolysis. The 5-methylene cyclic carbamates by either method are converted to 5-(chloromethylene) cyclic carbamates, using trichloroisocyanuric acid, followed by hydrolysis to a chloroketoamine. The chloroketoamine from the process of this invention additionally can be reacted with an organic acid chloride to form an amide compound which is useful as a fungicide.

公开(公告)号：EP0982292A3

公开(公告)日：2001-01-10

申请号：EP99306408.8

申请日：1999-08-13

Applicant: ROHM AND HAAS COMPANY

Inventor： Dubuisson-Brengel, Catherine ,  Rayle, Heather Lynnette

IPC: C07C241/04 ,  C07C243/24 ,  C07C241/02

CPC classification number: C07C241/04 ,  C07C243/38

Abstract: This invention provides a convenient process for the preparation of monoacylhydrazines from carboxylic acids or their salts and hydrazine or substituted hydrazine in the presence of a 1,3,5-triazine substituted with at least one chloro or fluoro. The resulting monoacylhydrazine can further be converted to a diacylhydrazine by effectively either repeating the reaction or through reaction with a carboxylic acid chloride.

公开(公告)号：EP0982292A2

公开(公告)日：2000-03-01

申请号：EP99306408.8

申请日：1999-08-13

Applicant: ROHM AND HAAS COMPANY

Inventor： Dubuisson-Brengel, Catherine ,  Rayle, Heather Lynnette

IPC: C07C241/04 ,  C07C243/24

CPC classification number: C07C241/04 ,  C07C243/38

Abstract: This invention provides a convenient process for the preparation of monoacylhydrazines from carboxylic acids or their salts and hydrazine or substituted hydrazine in the presence of a 1,3,5-triazine substituted with at least one chloro or fluoro. The resulting monoacylhydrazine can further be converted to a diacylhydrazine by effectively either repeating the reaction or through reaction with a carboxylic acid chloride.

Abstract translation: 本发明提供了在由至少一种氯或氟取代的1,3,5-三嗪存在下，从羧酸或其盐和肼或取代的肼制备单酰肼的方便方法。 通过有效地重复反应或通过与羧酸氯化物反应，可以将所得的单酰基肼进一步转化为二酰肼。

公开(公告)号：EP0872473A2

公开(公告)日：1998-10-21

申请号：EP98302710.3

申请日：1998-04-07

Applicant: ROHM AND HAAS COMPANY

Inventor： Rayle, Heather Lynnette ,  Roemmele, Renee Caroline ,  Stephens, Randall Wayne ,  Chong, Joshua Anthony ,  Abdesaken, Fereydon ,  Wu, Charles Chao

IPC: C07C221/00 ,  C07C225/06 ,  C07C225/10 ,  C07D263/38

CPC classification number: C07C221/00 ,  C07C225/06 ,  C07C225/10

Abstract: The present invention relates to a process for preparing 5-methylene cyclic carbamates either by cyclization of an alkynyl amine with carbon dioxide in the presence of a copper catalyst or by forming an isocyanate from a substituted acetoacetamide followed by hydrolysis. The 5-methylene cyclic carbamates by either method are converted to 5-(chloromethylene) cyclic carbamates, using trichloroisocyanuric acid, followed by hydrolysis to a chloroketoamine.
The chloroketoamine from the process of this invention additionally can be reacted with an organic acid chloride to form an amide compound which is useful as a fungicide.

Abstract translation: 本发明涉及一种通过在铜催化剂存在下使炔基胺与二氧化碳环化或通过由取代的乙酰乙酰胺形成异氰酸酯然后水解制备5-亚甲基环状氨基甲酸酯的方法。 通过任一方法将5-亚甲基环状氨基甲酸酯转化为5-（氯亚甲基）环状氨基甲酸酯，使用三氯异氰脲酸，然后水解成氯酮胺。 本发明方法中的氯代胺胺另外可与有机酰氯反应形成可用作杀真菌剂的酰胺化合物。

公开(公告)号：EP0872474A2

公开(公告)日：1998-10-21

申请号：EP98302711.1

申请日：1998-04-07

Applicant: ROHM AND HAAS COMPANY

Inventor： Rayle, Heather Lynnette ,  Roemmele, Renee Caroline ,  Stephens, Randall Wayne

IPC: C07C231/10 ,  C07C233/31 ,  C07C233/32 ,  C07C233/76 ,  C07D213/82 ,  C07D263/32 ,  C07D413/04

CPC classification number: C07D263/52 ,  C07C231/10 ,  C07C2601/14 ,  C07D263/14 ,  C07D263/32 ,  C07D413/04 ,  C07C233/76

Abstract: This invention relates to a process for the preparation of an α-chloroketone compound comprising the steps of

(i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline

(ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate
and
(iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone
wherein

Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,
R is a hydrogen atom or alkyl, and
R 1 and R 2 are each independently an alkyl or substituted alkyl group, or R 1 and R 2 together with the carbon atom to which they are attached form a cyclic structure.


Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.

公开(公告)号：EP0825173A1

公开(公告)日：1998-02-25

申请号：EP97306226.8

申请日：1997-08-15

Applicant: ROHM AND HAAS COMPANY

Inventor： Rayle, Heather Lynnette ,  Stephens, Randell Wayne

IPC: C07C67/317 ,  C07C69/76 ,  C07C45/65 ,  C07C49/76 ,  C07C51/377 ,  C07C63/68 ,  C07C231/12 ,  C07C253/30

CPC classification number: C07C253/30 ,  C07B61/00 ,  C07C45/65 ,  C07C51/377 ,  C07C67/317 ,  C07C231/12 ,  C07C49/78 ,  C07C63/06 ,  C07C63/70 ,  C07C69/76

Abstract: A method for synthesizing aromatic compounds by selectively dehalogenating aromatic starting materials is provided. Compounds may be prepared which are substituted with fluoro, chloro or bromo. The method may be used to remove halogen atoms from sites at which halogenation is not desired, and to form substantially pure halogenated compounds from mixtures of starting materials. The method uses a copper containing dehalogenation agent and an acid with the dehalogenation being controlled by a substituent such as a carboxylic acid, amide, ester, aldehyde, ketone or cyano on the aromatic ring.

Abstract translation: 提供了通过选择性脱卤芳族起始原料合成芳族化合物的方法。 可以制备被氟，氯或溴取代的化合物。 该方法可用于从不需要卤化的位置除去卤素原子，并从起始原料的混合物形成基本上纯的卤代化合物。 该方法使用含铜脱卤剂和在芳环上具有脱羧作用的酸由诸如羧酸，酰胺，酯，醛，酮或氰基的取代基控制。

公开(公告)号：EP0872474A3

公开(公告)日：2002-01-02

申请号：EP98302711.1

申请日：1998-04-07

Applicant: ROHM AND HAAS COMPANY

Inventor： Rayle, Heather Lynnette ,  Roemmele, Renee Caroline ,  Stephens, Randall Wayne

IPC: C07C231/10 ,  C07C233/31 ,  C07C233/32 ,  C07C233/76 ,  C07D213/82 ,  C07D263/32 ,  C07D413/04

CPC classification number: C07D263/52 ,  C07C231/10 ,  C07C2601/14 ,  C07D263/14 ,  C07D263/32 ,  C07D413/04 ,  C07C233/76

Abstract: This invention relates to a process for the preparation of an α-chloroketone compound comprising the steps of (i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline (ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone whereinZ is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene,R is a hydrogen atom or alkyl, andR1 and R2 are each independently an alkyl or substituted alkyl group, or R1 and R2 together with the carbon atom to which they are attached form a cyclic structure. Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.

Abstract translation: 本发明涉及一种制备α-氯代酮化合物的方法，包括以下步骤：（i）使炔基酰胺环化以形成5-亚甲基恶唑啉（ii）使用三氯异氰脲酸氯化5-亚甲基恶唑啉以产生氯代 恶唑啉中间体和（iii）用含水酸水解氯代恶唑啉中间体以产生所需的单氯代酮CHEM，其中Z是烷基或取代的烷基，芳基或取代的芳基，杂芳基或取代的杂芳基或亚苯基，R是氢 原子或烷基，R 1和R 2各自独立地为烷基或取代的烷基，或者R 1和R 2与它们所连接的碳原子一起形成环状结构。 此外，当R为氢原子时，可以通过调节反应条件方便地形成二氯酮。

公开(公告)号：EP0816328A3

公开(公告)日：2000-11-02

申请号：EP97304193.2

申请日：1997-06-16

Applicant: ROHM AND HAAS COMPANY

Inventor： Michelotti, Enrique Luis ,  Rayle, Heather Lynnette ,  Stephens, Randall Wayne ,  Zabrodski, William Joseph

IPC: C07C231/02 ,  C07C233/76 ,  C07C221/00 ,  C07C51/62 ,  C07C249/04 ,  C07C251/48

CPC classification number: C07C51/62 ,  C07C201/12 ,  C07C221/00 ,  C07C227/10 ,  C07C231/02 ,  C07C249/08 ,  C07C63/70 ,  C07C233/76 ,  C07C251/48 ,  C07C229/60 ,  C07C205/57 ,  C07C205/58 ,  C07C205/59 ,  C07C205/61 ,  C07C225/06

Abstract: Novel routes for the preparation of acetonylbenzamides are provided by the reaction of an amine and acyl chloride. Novel routes to various intermediates used in the manufacture of acetonylbenzamides are also disclosed.

公开(公告)号：EP0879819A1

公开(公告)日：1998-11-25

申请号：EP98303784.7

申请日：1998-05-14

Applicant: ROHM AND HAAS COMPANY

Inventor： Roemmele, Renee Caroline ,  Rayle, Heather Lynnette

IPC: C07D263/32 ,  C07C233/31 ,  C07C233/76

CPC classification number: C07D263/52 ,  C07C231/14 ,  C07D263/32 ,  C07D413/04 ,  C07C233/31 ,  C07C233/76

Abstract: This invention provides a process for the preparation of a 5-methylene-1,3-oxazoline from an alkyl ketone by reacting the alkyl ketone with an acetylating agent and an acid catalyst in an appropriate solvent and at an appropriate temperature. The resulting 5-methylene-1,3-oxazoline can be chlorinated and subsequently hydrolyzed to form an α-chloroketone which is useful as a fungicide.

Abstract translation: 本发明提供了通过使烷基酮与乙酰化剂和酸催化剂在合适的溶剂中和适当温度下由烷基酮制备5-亚甲基-1,3-恶唑啉的方法。 所得的5-亚甲基-1,3-恶唑啉可以被氯化并随后水解以形成可用作杀真菌剂的α-氯代酮。