Sumitomo Chemical Company, Limited

Nihon Medi-Physics Company, Limited

Naoyuki Takano

Shinzo Seko

Masayoshi Minai

Takayuki Higashii

Koichi Fujisawa

Kayoko Ueda

Yukari Fujimoto

Kazuyuki Tanaka

Koji Hagiya

Chizu Sekine

Yoshiaki Tsubata

Hideki Ushio

Motoo Hazama

Takeshi Tani

Yukihiro Honda

Akio Kurihara

Kyoko Endo

Isao Kurimoto

Shoji Toda

Daisaku Nakamura

Hiroshi Souda

Morio Yamamoto

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

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

There is disclosed a process for producing an amide compound, which process is characterized in that a compound having an amino group are reacted with a polyaminopolycarboxylic acid anhydride in the presence of the polyaminopolycarboxylic acid.

Process for producing an amide compound

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). 

Process for preparing thiazole by aminomethylation

There is provided a process for the production of carbonyl compounds, characterized by reacting a diol represented by the formula (1); wherein R, R, Rand Rare the same or different, and independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted aralkyloxycarbonyl group, carboxyl group or a hydrogen atom, or Rand Ror Rand Rare bonded together with the carbon atoms to which they are bonded to form a ring, provided that all of R, R, Rand Rare not hydrogen atoms simultaneously; with bromine or an inorganic bromine compound in the presence of a trivalent bismuth compound and a base to form carbonyl compounds represented by the formula (2); wherein Rand Rare as defined above; and the formula (3); wherein Rand Rare as defined above.

Process for production of carbonyl compounds

Process for producing carbonyl or hydroxy compound

A process for producing a purified aryl vinyl sulfone solution, characterized in that an aryl vinyl sulfone is crystallized from an organic solvent solution of a crude aryl vinyl sulfone to give a crystallization mixture, and a wet cake of the aryl vinyl sulfone obtained by the separation of the solution from the said mixture is dissolved in a solution-forming solvent selected from ethers of 4 to 8 carbon atoms, aromatic hydrocarbons of 6 to 10 carbon atoms, halogenated hydrocarbons of 1 to 6 carbon atoms, ketones of 3 to 8 carbon atoms, esters of 3 to 6 carbon atoms, and nitrites of 2 to 6 carbon atoms.

Process for producing aryl vinyl sulfone solution and use thereof

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.

Process for producing optically active azetidine-2-carboxylic acid

The present invention relates to trans-olefin compounds represented by the general formula (1) useful as an ingredient of liquid crystal composition, trans-olefin compounds useful as intermediate of pesticides, medical drugs, liquid crystal materials and the like, a process for producing those trans-olefin compounds, a liquid crystal composition containing the trans-olefin compound as an active ingredient, and a liquid crystal element using the liquid crystal composition. ##STR1## (In the general formula (1), R.sup.1, A.sup.1, A.sup.2, A.sup.3, Z and R.sup.2 are same as defined in the specification. Also, m, p, q, n, r, s and t are each an integer as defined in the specification.)

Trans-olefin compounds, method for production thereof, liquid crystal

A compound having an unsaturated side chain represented by the formula: ##STR1## in which A and B are the same and different and represent an aromatic or heterocyclic group or either one of A and B represents a single bond; X.sub.1, X.sub.2 and X.sub.3 are the same or different and represent a hydrogen atom or a lower alkyl group; R.sub.1 represents a saturated or unsaturated alkyl group which may be substituted with a halogen atom or an alkoxyalkyl group which may be substituted with a halogen atom; X represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond; n is an integer of 0 to 6; q is an integer of 1 to 15; p and s are each 0 or 1; and the asterisk * indicates an asymmetric carbon atom, which is useful as an intermediate of a liquid crystal or a monomer of a liquid crystalline polymer.

Compound having unsaturated side chain, process for preparing the same,

A compound having an unsaturated side chain represented by the formula: ##STR1## in which A and B are the same and different and represent an aromatic or heterocyclic group or either one of A and B represents a single bond; X.sub.1, X.sub.2 and X.sub.3 are the same or different and represent a hydrogen atom or a lower alkyl group; R.sub.1 represents a saturated or unsaturated alkyl group which may be substituted with a halogen atom or an alkoxyalkyl group which may be substituted with a halogen atom; X represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.ident.C-- or a single bond; n is an integer of 0 to 6; q is an integer of 1 to 15; p and s are each 0 or 1; and the asterisk * indicates an asymmetric carbon atom, which is useful as an intermediate of a liquid crystal or a monomer of a liquid crystalline polymer.

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Ibaraki, Japan

Naoyuki Takano