M-Phenylenediamine → HCID 22765670, compound
Reaction equation
Cl[C:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[N:14]=[C:13]3[CH:15]=[CH:16][C:17](C(Cl)=O)=[CH:18][C:12]3=[N:11]2)=[CH:6][CH:5]=1)=[O:3].[CH3:22][O:23]C(=O)C1C=CC(N)=CC=1.C1(N)C=CC=C([NH2:39])C=1>N1C=CC=CC=1>[CH3:22][O:23][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[N:14]=[C:13]3[CH:15]=[CH:16][C:17]([NH2:39])=[CH:18][C:12]3=[N:11]2)=[CH:6][CH:5]=1)=[O:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
the 2-(4-chlorocarbonylphenyl)-5-chlorocarbonylbenzotriazole used in Examples 1 to 9 was prepared in the following way: p-aminobenzoic acid methyl ester is diazotised in the customary manner and the diazo compound is coupled with m-phenylenediamine. The resulting crude azo dyestuff is oxidised in hot pyridine with Cu-II acetate to give 2-(4-methoxycarbonylphenyl)-5-aminobenztriazole with a melting point of 240° C, 135 g of this amine are dissolved in 375 ml of concentrated sulphuric acid and diazotised at 15° to 20° C with nitrosylsulphuric acid. The diazonium salt solution is discharged onto 2.5 kg of ice; the diazonium salt is filtered off and suspended in 800 ml of ice water. This suspension is added in small portions to a solution of 50 g of copper-I cyanide, 75 g of sodium cyanide, 500 ml of water and 250 ml of dimethylformamide. A brown product separates out, with vigorous evolution of gas, and this product can be purified by recrystallisation from o-dichlorobenzene and dimethylformamide; melting point 265° C, blue-fluorescent. The product has the formula ##STR16## and is subjected to alkaline saponification in aqueous glycol monomethyl ether. The product of the formula ##STR17## which melts at 146°-148° C is obtained by boiling in a large excess of thionyl chloride.
Workup
- customwas prepared in the following way
Sources & evidence
- ORD record
- ord-6da0a9fdac5e418595f25f979d1b11fd
- Source dataset
- uspto-grants-1978_10
- Patent number
- US04119634
Reaction notes
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