Sulfuric Acid → 3-(N-methylamino)aniline-4-sulfonic acid
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[C:4]([NH2:12])[CH:3]=1.[OH-].[Na+].S(OC)(O[CH3:19])(=O)=O.S(=O)(=O)(O)O>C(O)=O.O>[CH3:19][NH:12][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[S:8]([OH:11])(=[O:9])=[O:10])[NH2:1]Participants
7
Conditions
- Temperature
- 30 °C
Procedure
97 g of 1,3-diaminobenzene-4-sulfonic acid were stirred with 250 ml of water and, after the addition of 38 ml of 98% w/w formic acid, boiled at 95°-100° C. The mixture was then cooled to 30° C., and 65 g of ice were added, the pH being adjusted to 6.5 to 7.0 with 60.5 ml of 50% w/w caustic soda solution. There were then added 45 ml of 50% w/w caustic soda solution and 70 ml of dimethyl sulfate, and stirring was continued for 30 minutes. The mixture was then acidified with 43 ml of 96% w/w sulfuric acid and stirred at 100° C. for 3 hours. The mixture was then cooled, and the precipitated 3-(N-methylamino)aniline-4-sulfonic acid was isolated by filtration.
Workup
- stirringstirred at 100° C. for 3 hours
- temperatureThe mixture was then cooled
Sources & evidence
- ORD record
- ord-2a334297f8a9418bafae4ddfedaadc55
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05117050
Reaction notes
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