公开(公告)号：JPS61189273A

公开(公告)日：1986-08-22

申请号：JP3089385

申请日：1985-02-19

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YASUMOTO MASAHIKO ,  YANAGIYA KOSHIN ,  KURABAYASHI MASAHIRO

IPC: C07D409/04 ,  C07D213/00 ,  C07D235/00 ,  C07D235/06 ,  C07D307/00 ,  C07D333/00 ,  C07D401/04 ,  C07D405/04

Abstract: PURPOSE:To obtain the titled substance useful as pharmaceuticals, agricultural chemicals, etc. on one step, in high yield, without using a reaction reagent which might cause the environmental pollution, from inexpensive raw materials, by reacting a nitrile with o-phenylenediamine in the presence of an alcohol under pressure. CONSTITUTION:The compound of formula III is produced by reacting the nitrile of formula I (R1 is alkyl, aryl, aralkyl or heterocyclic group which may have substituent group) with the o-phenylenediamine of formula II (R2 is same as R1 or H, halogen, nitro or N-substituted amino) in the presence of an alcohol under high pressure (higher the better; usually 1,000-9,000kg/cm ) at 30-150 deg.C. The molar ratio of the nitrile of formula I to the compound of formula II is preferably 1:5-5:1, and the amount of the alcohol is 0.1-10mol per 1mol of the nitrile.

公开(公告)号：JPS63221171A

公开(公告)日：1988-09-14

申请号：JP5479087

申请日：1987-03-10

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YASUMOTO MASAHIKO ,  YANAGIYA KOSHIN ,  SHIBUYA ISAO ,  SEKIGUCHI TATSUO

IPC: C09B11/00 ,  C07C1/32 ,  C07C15/16 ,  C09B11/14

Abstract: PURPOSE:To obtain the title compd. which is a colorless crystal and has a high purity in a high yield without causing environmental pollution, by subjecting an arom. aldehyde and an arom. diamine to a dehydration-condensation reaction in the presence of optionally, a small amount of a reaction accelerator under high pressure. CONSTITUTION:An arom. aldehyde (A) such as benzaldehyde or a dialkylamino-, alkoxy-, alkyl-, NO2 or halogen-substd. benzaldehyde and an arom. amine (B) such as N,N-dialkylaniline, N-alkylaniline, aniline or a substitution compd. thereof are subjected to a dehydration-condensation reaction in the presence of a optionally, 0.1-50mol.% (based on the amount of the component A) of a reaction accelerator such as protonic acid, Lewis acid, etc. under a high pressure of 1,000-9,000kg/cm .

公开(公告)号：JPS63218672A

公开(公告)日：1988-09-12

申请号：JP5274887

申请日：1987-03-07

Applicant: AGENCY IND SCIENCE TECHN

Inventor： TAGUCHI YOICHI ,  YANAGIYA KOSHIN ,  SHIBUYA ISAO ,  SUHARA YASUO

IPC: C07D327/04 ,  B01J31/02 ,  C07B61/00 ,  C07D339/06

Abstract: PURPOSE:To obtain the titled substance useful as a synthetic intermediate for tetrathiafulvalene which is a charge-transfer complex, intermediate material for physiologically active substance or the like in one stage and good yield, by reacting an epoxide with CS2 in the presence of a base under high pressure. CONSTITUTION:An epoxide expressed by formula I (R is alkyl or aryl; R and R are alkyl or H) is reacted with CS2 in the presence of a base (preferably tert. amine) at high pressure of 500-9,000kg/cm2 and room temperature - 120 deg.C for 5-50hr to provide the aimed compounds expressed by formula II and formula III.

公开(公告)号：JPS62209068A

公开(公告)日：1987-09-14

申请号：JP5207386

申请日：1986-03-10

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIBUYA ISAO ,  YANAGIYA KOSHIN ,  YASUMOTO MASAHIKO

IPC: C07D271/06

Abstract: PURPOSE:To readily obtain the titled substance useful as an anesthetic agent, analgesic agent, antitussive agent, etc., in good yield, by reacting an aldoxime with a disubstituted cyanamide. CONSTITUTION:An aldoxime expressed by formula I (R is alkyl, aryl, etc.) is reacted with a disubstituted cyanamide expressed by formula II (R and R are alkyl, aryl, etc., or may together link at the terminals thereof), as neces sary, in an inert organic solvent, e.g. THF, benzene, etc., at 50-150 deg.C to afford a 5-amino-3-substituted 1,2,4-oxadiazole expressed by formula III and 5-(N,N- disubstituted guanidino)-3-substituted 1,2,4-oxadiazole (novel substance) expressed by formula IV. In order to mainly obtain the compound expressed by formula III, the compounds expressed by formulas I and II are reacted at =1:2 above-mentioned molar ratio of the compounds expressed by formula I to II under a high pressure for a long time.

公开(公告)号：JPS61186372A

公开(公告)日：1986-08-20

申请号：JP2727185

申请日：1985-02-14

Applicant: AGENCY IND SCIENCE TECHN

Inventor： YASUMOTO MASAHIKO ,  YANAGIYA KOSHIN ,  KURABAYASHI MASAHIRO

IPC: C07D417/04 ,  C07D213/00 ,  C07D277/00 ,  C07D277/64 ,  C07D307/00

Abstract: PURPOSE:To obtain a benzothiazole useful as pharmaceuticals and agricultural chemicals, etc. from an inexpensive raw material, in one step and high yield, economically on an industrial scale, by reacting a specific nitrile with 2- aminothiophenol in the presence of an alcohol under pressure. CONSTITUTION:The objective compound of formula II such as 2-(t-butyl)- benzothiazole can be produced by reacting the nitrile of formula R1CN (R1 is alkyl, aryl, aralkyl or heterocyclic group which may have substituent group) with the 2-aminothiophenol of formula I (R2 is same as R1 or H, halogen or N-substituted amino) at a molar ratio of 1:5-5:1 in the presence of an alcohol at 30-150 deg.C for 5-50hr under the pressure of 1,000-9,000kg/cm . The alcohol is a lower alcohol such as methanol, ethanol, etc., and is preferably methanol. The amount of the alcohol is 0.1-10mol per 1mol of the nitrile.

公开(公告)号：JPS63218673A

公开(公告)日：1988-09-12

申请号：JP5370187

申请日：1987-03-09

Applicant: AGENCY IND SCIENCE TECHN

Inventor： SHIBUYA ISAO ,  YANAGIYA KOSHIN ,  YASUMOTO MASAHIKO

IPC: C07D339/06 ,  B01J31/02 ,  C07B61/00 ,  C07D409/04

Abstract: PURPOSE:To obtain the titled compound which is an intermediate for synthetic compound such as medicine in one process and high yield without by-product, by using an acetylene compound, carbon disulfide and sulfur which are simple raw material and reacting the acetylene compound with the carbon disulfide and sulfur under high pressure in the presence of a base. CONSTITUTION:Acetylenes expressed by formula I (R and R are inert substituent groups or H), carbon disulfide and sulfur are used as raw material and the acetylenes are reacted with the carbon disulfide and sulfur under high pressure in the presence of a base, preferably triethylamine, pyridine, N,N- dimethylaniline, etc., preferably at room temperature - 100 deg.C normally for 5-50hr to provided the aimed compound expressed by formula II. Commercial products may be directly use as the carbon disulfide and sulfur which are the above-mentioned raw material and the carbon disulfide is preferably used in excess amount, since the carbon disulfide is a raw material for dissolving sulfur. Although higher pressure is preferred, the pressure is suitable normally in the range of 500-9,000kg/cm .

公开(公告)号：JPS62207268A

公开(公告)日：1987-09-11

申请号：JP4936686

申请日：1986-03-06

Applicant: AGENCY IND SCIENCE TECHN

Inventor： TAGUCHI YOICHI ,  YANAGIYA KOSHIN ,  SHIBUYA ISAO ,  SUHARA YASUO

IPC: C07D339/06

Abstract: PURPOSE:To obtain the titled compound useful as an intermediate for tetrathiafulvalene (electric charge transfer complex) or an intermediate substance for physiological active substance simply and in high yield, by reacting thiirane compound with carbon disulfide in the presence of a base at a high temperature. CONSTITUTION:A thiirane compound shown by formula I (R is alkyl or aryl; R and R are alkyl or H) is reacted with carbon disulfide in the presence of a base such as tertiary amine, e.g. triethylamine, pyridine, etc. at high pressure of 500-9,000kg/cm at room temperature -100 deg.C to give the aimed compound shown by formula II in high yield and efficiently. The compound shown by formula I can be readily synthesized from a corresponding epoxide and thiourea or potassium thiocyanate and carbon dioxide is inexpensively sold on the market.