O-Toluidine → Benzenesulfono-o-toluidide

HRID 326009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 326009
[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]

Komponenten

3

Edukt 2

HCID 7242O-ToluidineHCID 7369Benzenesulfonyl chloride

Produkt 1

HCID 87657Benzenesulfono-o-toluidide

Versuchsvorschrift

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

Aufarbeitung

  1. customThe so far single industrially feasible synthesis

Quellen und Nachweise

ORD-Eintrag
ord-e8752a481a614c8cb4ffb13e52459e83
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04443630

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