Methanol → 1-Methoxy-1-(2-methoxyphenyl)-2-phenylhydrazine
Reaction equation
[SH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11](=[N:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1OC)[O-:12].[CH3:22]O>>[CH3:22][O:12][N:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH3:3])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
4
Procedure
90 parts of an aqueous solution of technical sodium hydrosulfide containing 35 percent NaHS and 4 percent NasS2O3 were added to a mixture comprising 51.6 parts of 2,2'-dimethoxyazoxybenzene in 155 parts methanol at room temperature within 5 hours. Subsequently, the reaction mixture was refluxed at 70° C to 75° C for 2 1/2 hours while the pH was maintained between 8.5 and 9.4. After this period the absence of the starting material was confirmed and the reaction mixture was cooled down to 0° C to 5° C, the reduced product that precipitated filtered off and washed with water until alkali-free. After drying below 70° C, 35 parts of 2,2'-dimethoxyhydrazobenzene of a melting point of 100° C to 102° C were obtained, this representing a commercially acceptible grade in a yield of 72 percent of theory.