Reaction equation
N([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[N:5]([CH3:7])[CH3:6])=O.C[N:13](C)C1C=CC=CC=1.N([O-])=O.[ClH:24]>>[NH2:13][C:10]1[CH:9]=[CH:8][C:4]([N:5]([CH3:7])[CH3:6])=[CH:3][CH:11]=1.[ClH:24]Participants
Procedure
In step (a), nitrosodimethylaniline is prepared from dimethylaniline by treatment with nitrite (NaNO2) in aqueous acid (HCl) solution. In step (b), the nitroso compound is reduced to form p-aminodimethylaniline in aqueous acid (HCl) solution using zinc dust solution. In steps (c), (d), and (e), the p-aminodimethylaniline is oxidized in aqueous acid solution with another molecule of dimethylaniline, and simultaneously a thiosulfonic acid group is introduced; the ring is then closed using manganese dioxide or copper sulfate. More specifically, a clear neutral solution of p-aminodimethylaniline is acidified (H2SO4), and a non-reducing zinc chloride solution is added (ZnCl2 with Na2Cr2O7). Aluminium thiosulfate (Al2(S2O3)3) and sodium thiosulfate (Na2S2O3) are added. Sodium dichromate (Na2Cr2O7) is added. The mixture is heated and aerated. Dimethylaniline is added. Sodium dichromate (Na2Cr2O7) is added. The mixture is heated, and becomes dark greenish-blue in colour due to the formation of the thiosulfonic acid of Bindschedler green. Manganese dioxide or copper sulfate is added, and the mixture heated, and the dye precipitates from the concentrated zinc chloride solution.
Sources & evidence
- ORD record
- ord-654e999f690d4b79ade88aea9c4b4b02
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440821B2
Linked notes
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