公开(公告)号：JPS5890563A

公开(公告)日：1983-05-30

申请号：JP18689481

申请日：1981-11-24

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU ,  KAKEYA NOBORU ,  YOKOO YASUHIKO

IPC: C07D239/557 ,  C07D239/54

Abstract: PURPOSE:The reaction of an alkali metal salt of 5-carboxyorotic acid with a halogenating reagent is followed by treatment of the product with an acid to give the titled compound, especially 5-iodoorotic acid, used as a medicine or its starting material, in high yield. CONSTITUTION:A halogenating reagent is added as much, or in the form of an aqueous solution or solution in a inert organic solvent, to an aqueous solution of an alkali metal salt of 5-carboxyorotic acid of formulaI(M is Li, Na, K) and their reaction is effected by heating at 0-100 deg.C and the resultant reaction product is acidified with a mineral acid at 0-30 deg.C to give the objective compound. As a halogenating reagent, is used Br2, I2 or N-chlorosuccinimide. The compound of formulaIis obtained by making 3-amino-1,4-bis(alkoxycarbonyl) maleimide of formula III (R , R are 1-4C alkyl) react with an alkali hydroxide in water at room temperature or under heating and acidifying the reaction mixture with a mineral acid.

公开(公告)号：JPS5888361A

公开(公告)日：1983-05-26

申请号：JP18689381

申请日：1981-11-24

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU ,  YOKOO YASUHIKO

IPC: C07D207/456

Abstract: NEW MATERIAL:3-Amino-1,4-bis(alkoxycarbonyl)maleimide compound of formulaI (R and R are 1-4C alkyl). EXAMPLE:3-Amino-1,4-bis(ethoxycarbonyl)maleimide. USE:Phramaceuticals, agricultural chemicals, and their intermediates. PROCESS:The compound of formulaIcan be prepared by reacting the alkoxyiminoacetic acid ester of formula II (R and R are 1-4C alkyl) with the N- (alkoxycarbonyl)acetylcarbamic acid ester of formula III in the absence of solvent or in an organic solvent at 20-150 deg.C for 1-50hrs.

公开(公告)号：JPS5888360A

公开(公告)日：1983-05-26

申请号：JP18689281

申请日：1981-11-24

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU ,  FUJIMURA SUSUMU ,  MATSUO FUMIO

IPC: C07D207/456 ,  A01N37/32

Abstract: NEW MATERIAL:The compound of formulaI(R is 1-4C alkyl or halogen; R is phenyl substituted with 1-4C alkyl or alkoxy; R is 2-5C alkoxycarbonyl). EXAMPLE:1-(p-Chlorophenyl)-3-ethoxycarbonyl-4-(p-toluidino)maleimide. USE:Agricultural chemicals, pharmaceuticals and their intermediates. PROCESS:The compound of formulaIcan be prepared by reacting the carbamoylaminomaleimide compound of formula II with a tertiary amine in an inert organic solvent under essentially anhydrous conditions at 20-150 deg.C for 1-50hrs.

公开(公告)号：JPS5862164A

公开(公告)日：1983-04-13

申请号：JP15949781

申请日：1981-10-08

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU ,  OKIMOTO KIYOMI

IPC: C07D233/96

Abstract: PURPOSE:To obtain the titled substance useful as a drug, agricultural chemical, etc. in high yield, by reacting a reaction product of an alkoxyiminoacetic ester with an amine with an isocyanate in the presence of a tertiary amine and/or quaternary ammonium fluoride. CONSTITUTION:A compound shown by the formulaI(R and R are 1-4C alkyl) is reacted with a compound shown by the formula II (R is 1-4C alkyl, etc.) in the presence or absence of an inert organic solvent (alcohol, aromatic hydrocarbon, etc.) at 0-150 deg.C to give a compound shown by the formula V, preferably after the removal of an alcohol as a by-product from the reaction product mixture, the compound is reacted with a compound shown by the formula III (R is 1-4C alkyl, etc.) in the presence of a tertiary amine (e.g., trimethylamine) and/or quaternary ammonium fluoride at 20-100 deg.C for 1-30hr, to give a compound shown by the formula IV.

公开(公告)号：JPS5855455A

公开(公告)日：1983-04-01

申请号：JP15302581

申请日：1981-09-29

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU ,  FUJIMURA SUSUMU ,  YOKOO YASUHIKO

IPC: A01N37/32 ,  A01N37/34 ,  C07D207/456

Abstract: NEW MATERIAL:The aminomaleimide of formulaI[R is H, 1-4C alkyl, or group of formula II (R is 1-4C alkyl or halogen; m is 0-3); X is 2-5C alkoxycarbonyl, 2-5C aliphatic acyl, benzoyl, or cyano]. EXAMPLE:3-Amino-4-cyanomaleimide. USE:Useful as pharmaceuticals, pesticides and their intermediates. PROCESS:The compound of formulaIcan be prepared by reacting a cyanoformic acid ester of formula III (R is 1-4C alkyl) with an amide of formula IV in the presence of zinc chloride and a tert-amine preferably in a solvent such as benzene, methylene chloride, etc. at 20-100 deg.C, and treating the resultant reaction product with an acidic aqueous solution such as hydrochloric acid, p-toleunesulfonic acid, etc.

公开(公告)号：JPS5446739A

公开(公告)日：1979-04-12

申请号：JP11329077

申请日：1977-09-22

Applicant: UBE INDUSTRIES

Inventor： MAZAKI MITSUO ,  MATSUNAMI RIYOU ,  KITA JIYUNICHIROU ,  FUJIMURA SUSUMU

IPC: B01J31/00 ,  C07B61/00 ,  C07C51/00 ,  C07C51/60 ,  C07C63/00 ,  C07C67/00

Abstract: PURPOSE:To prepare an aromatic carboxylic acid chloride, by reacting an aromatic carboxylic acid or its anhydride with carbon monoxide and chlorine in one stage in the presence of phosphine oxide and/or phosphine chloride. CONSTITUTION:An aromatic carboxylic acid, e.g. benzoic acid, etc. or its anhydride is reacted with carbon monoxide and chlorine in the presence of phosphine oxide, e.g. tributyl phosphine oxide, etc. and/or phosphine chloride, e.g. trimethylphosphine dichloride, etc. as a catalyst in such a range that the product of (the number of PO or PCl2 groups contained in one molecule of the catalyst) and (the number of moles of the catalyst) is 1/200-1/10 based on the product of (the number of carboxylic acid groups or its anhydride groups) and (the number of moles of carboxylic acid or its anhydride) to give an aromatic carboxylic acid chloride, e.g. benzoic acid chloride, etc. EFFECT:High toxic phosgene need not be used.

公开(公告)号：JPS53141290A

公开(公告)日：1978-12-08

申请号：JP5439477

申请日：1977-05-13

Applicant: UBE INDUSTRIES

Inventor： MAZAKI MITSUO ,  FUKUI KIYOSHI ,  KITA JIYUNICHIROU

IPC: C07D201/02

Abstract: PURPOSE:To prepare ?-caprolactam in high purity and high yield without formation of ammonium sulfate by hydrogenation of 1,3-dihydro-2H-azepin-2-ones in the presence of a cheap nickel catalyst.

公开(公告)号：JPS60218364A

公开(公告)日：1985-11-01

申请号：JP7290684

申请日：1984-04-13

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU

IPC: C07C257/14 ,  C07C67/00 ,  C07C239/00 ,  C07C257/16 ,  C07C257/18

Abstract: NEW MATERIAL:A compound of formula I [R is 1-20C alkyl, 2-5C alkenyl, 5-7C cycloalkyl, 7-10C aralkyl or formula II (R is 1-4C alkyl), 1-4C alkoxyl, halogen, etc.; n is an integer 0, 1, 2 or 3)]. EXAMPLE:N-Isopropylamidinecarboxamide. USE:Useful as agricultural chemicals medicines and intermediates therefor. PREPARATION:An alkoxyiminoacetamide of formula III (R is lower alkyl) is reacted with a primary amine of the formula R -NH2 in the presence of a solvent, e.g. benzene, at 20-120 deg.C for 1-100hr to give the aimed compound of formula I . Preferably, the same alcohol as an alcohol formed as a by-product by the reaction is used as the reaction solvent for facilitating separation and recovery of the reaction solvent after the reaction.

公开(公告)号：JPS5890564A

公开(公告)日：1983-05-30

申请号：JP18689581

申请日：1981-11-24

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU ,  YOKOO YASUHIKO

IPC: C07D239/557 ,  C07D239/54

Abstract: NEW MATERIAL:A 5-cyanoorotic acid ester of formulaI(R is 1-4C alkyl, allyl, cyclohexyl, benzyl, phenyl; R is 1-4C alkyl). EXAMPLE:Ethyl 5-cyano-1-ethylorotinate. USE:Medicines, farm chemicals and their intermediate. PREPARATION:Under substantially anhydrous conditions, the reaction between an alkoxyiminoacetic ester of formula II (R is the same as R ) and an N- cyanoacetylcarbamic ester of formula III (R are the same as R , R ) is carried out in the absence or presence of a solvent at 20-100 deg.C for 1hr to 5 days to give the compound of formulaI.

公开(公告)号：JPS5890543A

公开(公告)日：1983-05-30

申请号：JP18689681

申请日：1981-11-24

Applicant: UBE INDUSTRIES

Inventor： FUKUI KIYOSHI ,  KITA JIYUNICHIROU ,  YOKOO YASUHIKO

IPC: A01N47/12 ,  A01N37/32 ,  A01N43/36 ,  C07C67/00 ,  C07C239/00 ,  C07C271/22 ,  C07D207/456

Abstract: NEW MATERIAL:Compounds of formulaIand II (R and R are 1-4C alkyl). EXAMPLE:1 -Amino-2-cyano- 1 -mthoxycarbonyl-2-[ N-( methoxycarbonyl )carbamoyl]-ethylene. 3-Amino-4-cyano-1-(methoxycarbonyl)maleimide. USE:Medicine, agricultural chemical and their intermediate. PREPARATION:The reaction of an alkoxyiminoacetic ester of formula (R is 1-4C alkyl) with an N-cyanoacetylcarbamic ester of formula IV gives compounds of formulaIand II. The reaction is carried out in an organic solvent such as benzene at 0-30 deg.C to form mainly a compound of formulaIand, when the reaction temperature is raised or a base such as a compound of formula V is added to the reaction mixture, the cyclization reaction from a compound of formulaIto the one of formula II is promoted.