The invention provides novel methods for preparing indolinobenzodiazepine dimer compounds and their synthetic precursors.

The invention provides novel methods for preparing indolinobenzodiazepine dimer compounds and their synthetic precursors.

The invention provides novel methods for preparing indolinobenzodiazepine dimer compounds and their synthetic precursors.

A production method in which a mercaptophenol compound is obtained using an industrially preferred sulfur atom introduction reaction, and intermediate compounds of the mercaptophenol compound are provided. A method for producing a mercaptophenol compound in which a phenyl carbamate compound is produced using a phenol compound as a raw material, and then a sulfur atom is regioselectively introduced by a reaction with sulfur monochloride, and a phenyl mercaptocarbamate compound is produced as an intermediate.

A production method in which a mercaptophenol compound is obtained using an industrially preferred sulfur atom introduction reaction, and intermediate compounds of the mercaptophenol compound are provided. A method for producing a mercaptophenol compound in which a phenyl carbamate compound is produced using a phenol compound as a raw material, and then a sulfur atom is regioselectively introduced by a reaction with sulfur monochloride, and a phenyl mercaptocarbamate compound is produced as an intermediate.

Provided is a method for producing a polythiol compound, including reacting 2-mercaptoethanol with an epihalohydrin, wherein the reaction is carried out in the presence of a halide selected from the group consisting of a 2,3-dihalogeno-1-propanol and an allyl halide, and an amount of the halide in the reaction is more than 0.50% by mass and 10.00% by mass or less with respect to the total amount of the halide and the epihalohydrin. Also provided are a method for producing a curable composition, including producing a polythiol compound by the abovementioned production method, and a method for producing a cured product, including producing a curable composition by the abovementioned production method.

Provided is a method for producing a polythiol compound, including reacting 2-mercaptoethanol with an epihalohydrin, wherein the reaction is carried out in the presence of a halide selected from the group consisting of a 2,3-dihalogeno-1-propanol and an allyl halide, and an amount of the halide in the reaction is more than 0.50% by mass and 10.00% by mass or less with respect to the total amount of the halide and the epihalohydrin. Also provided are a method for producing a curable composition, including producing a polythiol compound by the abovementioned production method, and a method for producing a cured product, including producing a curable composition by the abovementioned production method.

A production method in which a mercaptophenol compound is obtained using an industrially preferred sulfur atom introduction reaction, and intermediate compounds of the mercaptophenol compound are provided. A method for producing a mercaptophenol compound in which a phenyl carbamate compound is produced using a phenol compound as a raw material, and then a sulfur atom is regioselectively introduced by a reaction with sulfur monochloride, and a phenyl mercaptocarbamate compound is produced as an intermediate.

A production method in which a mercaptophenol compound is obtained using an industrially preferred sulfur atom introduction reaction, and intermediate compounds of the mercaptophenol compound are provided. A method for producing a mercaptophenol compound in which a phenyl carbamate compound is produced using a phenol compound as a raw material, and then a sulfur atom is regioselectively introduced by a reaction with sulfur monochloride, and a phenyl mercaptocarbamate compound is produced as an intermediate.

The present invention includes methods for making and isolating N-acetylcysteine amide, (2R,2R)-3,3-disulfanediyl bis(2-acetamidopropanamide, diNACA), intermediates and derivatives thereof comprising: contacting cystine with an alcohol and a chlorinating reagent to form an organic solution containing L-cystine dimethylester dihydrochloride; combining dried or undried L-cystine dimethylester dihydrochloride with a triethylamine, an acetic anhydride, and an acetonitrile to form a di-N-acetylcystine dimethylester; mixing dried di-N-acetylcystine dimethylester with ammonium hydroxide to form a di-N-acetylcystine amide (diNACA); and separating dried di-N-acetylcystine dimethylester into N-acetylcysteine amide with dithiothreitol, triethylamine and an alcohol.