Sulfuric Acid → 3,3'-[(Phenylazanediyl)bis(methylene)]di(benzene-1-sulfonic acid)
Reaction equation
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:22](=[O:26])(=[O:25])([OH:24])O.[OH:27][S:28](O)(=[O:30])=[O:29].O=S(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>>[S:22]([C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([S:28]([OH:30])(=[O:29])=[O:27])[CH:7]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([OH:24])(=[O:26])=[O:25]Participants
Procedure
With stirring, 150.0 g of N,N-dibenzylaniline was added slowly over approximately two hours to 425.0 g of 100 percent sulfuric acid while maintaining a temperature in the range of 25° to 30° C. The resulting solution was set aside at ambient temperature for approximately fourteen hours. Then, 165 g of 65 percent oleum was added to the solution with stirring while maintaining a temperature in the range of 25° to 30° C. using an ice water bath. The resulting solution was stirred approximately 19 hours at ambient temperature and then was poured slowly onto ice with stirring. Sufficient sodium carbonate was added gradually to the drowned mixture to adjust the pH to approximately 7.0 and thus obtaining a solution of N,N-bis(3-sulfobenzyl)aniline.
Workup
- temperaturewhile maintaining a temperature in the range of 25° to 30° C
- waitThe resulting solution was set aside at ambient temperature for approximately fourteen hours
- stirringwith stirring
- temperaturewhile maintaining a temperature in the range of 25° to 30° C.
- stirringThe resulting solution was stirred approximately 19 hours at ambient temperature
- additionwas poured slowly onto ice
- stirringwith stirring
Sources & evidence
- ORD record
- ord-fbc1222f78704ad58f2fcef3d994df3b
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04632783
Reaction notes
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