O-Toluidine → Benzenesulfono-o-toluidide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[C:9]1([S:15](Cl)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][S:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:17])=[O:16]Participants
3
Procedure
The so far single industrially feasible synthesis is described by BIOS Final Report 986/2, No. 167, pages 297-306, and involves acylating 2-aminotoluene with benzenesulfonyl chloride to give N-(2-methylphenyl)-benzenesulfonamide, nitrating the latter in chlorobenzene, and, finally, splitting off the protective group by hydrolysis and isolating 2-amino-5-nitrotoluene. This synthesis gives a yield of about 75% of theory. In addition to this unsatisfactory yield, the numerous process stages and the associated consumption of chemicals, this process harbors further grave disadvantages which render its industrial application problematical from a processing and an ecological point of veiw
Workup
- customThe so far single industrially feasible synthesis
Sources & evidence
- ORD record
- ord-e8752a481a614c8cb4ffb13e52459e83
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04443630
Reaction notes
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