Sumitomo Chemical Company, Limited

Sumitomo Seika Chemicals Co., Ltd.

Shinzo Seko

Toshiya Takahashi

Naoto Konya

Naoyuki Takano

Motoo Hazama

Atsushi Furutani

Kazuyuki Tanaka

Hideki Ushio

Yukihiro Honda

Kazutaka Kimura

Toru Sakamoto

Noriyuki Doi

Kenji Saito

Isao Kurimoto

Akihiko Nakamura

Hiroshi Souda

Kunihito Miyake

Takashi Miki

Akio Kurihara

Hirotada Kakiya

Nobuhiro Tani

Morio Yamamoto

Kazuyoshi Yamashita

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.

Method for producing thiazole compound

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.

Method for selectively producing primary amine compound

A process for producing a thiazole compound of the formula (3): wherein Xis a hydrogen atom or a halogen atom, which comprises reacting a compound of the formula (1): wherein Xis as defined above, and Xrepresents a halogen atom, with ammonia and formaldehyde to obtain a hexahydrotriazine compound of the formula (2): wherein Xis 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 Xis as defined above.

Process for producing thiazole compound

A process for the production of an alcohol compound represented by the formula (3): wherein X, X, X, X, Z, R and n are as defined below, comprising reacting a phenol represented by the formula (1): wherein X, X, Xand Xindependently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Z represents an oxygen atom or a sulfur atom; and R represents an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group which may be substituted by a halogen atom, with a haloalcohol represented by the formula (2): wherein Y represents a chlorine atom or a bromine atom; and n represents an integer of 2 or 3, in a biphase system composed of a water-immiscible organic solvent and an aqueous alkali metal hydroxide solution in the presence of a phase-transfer catalyst.

Process for production of alcohol compound

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, Rand Rindependently 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; Rrepresents 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, R, Rand Rare as defined above.)  

Method for producing primary amine compound

A process for the production of an alcohol compound represented by the formula (3): wherein X, X, X, X, Z, R and n are as defined below, comprising reacting a phenol represented by the formula (1): wherein X, X, Xand Xindependently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Z represents an oxygen atom or a sulfur atom; and R represents a halogen-substituted alkenyl group, with a haloalcohol represented by the formula (2): wherein Y represents a chlorine atom or a bromine atom; and n represents an integer of 2 or 3, in a biphase system composed of a water-immiscible organic solvent and an aqueous alkali metal hydroxide solution in the presence of a phase-transfer catalyst.

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

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Toyonaka, Japan

Shinzo Seko