Sulfamic Acid → 2-Amino-4-methyl-5-nitrobenzenesulfonic acid

HRID 1076767

Reaktionsgleichung

Reaktionsgleichung von HRID 1076767
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.ClC1C=CC=CC=1.[S:19](=[O:23])(=[O:22])([OH:21])N>CN1CCCC1=O>[NH2:1][C:2]1[C:7]([S:19]([OH:23])(=[O:22])=[O:21])=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1

Komponenten

5

Edukt 3

HCID 5987Sulfamic AcidHCID 7964ChlorobenzeneHCID 118984-Nitro-m-toluidine

Produkt 1

HCID 30162832-Amino-4-methyl-5-nitrobenzenesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

18.3 g of 1-amino-3-methyl-4-nitrobenzene, 120 ml of chlorobenzene, 24 g of sulphamic acid and 12 ml of 1-methylpyrrolid-2-one are warmed to 120°C whilst stirring. The reaction mixture is stirred for 8 hours at this temperature. After cooling, the reaction mixture is filtered and the residue is washed with trichloroethylene and recrystallised from 200 ml of water. The crystals which have precipitated are filtered off, suspended in 100 ml of trichloroethylene, stirred for one hour at 75°C, separated from the organic solvent by filtration and dried at 80°C. 25 g (84% of theory) of yellow crystals, which according to thin layer chromatography are a single substance, of 1-amino-3-methyl-4-nitro-benzene-6 -sulphonic acid in the form of its ammonium salt [melting point 290° C (decomposition)]are obtained.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for 8 hours at this temperature
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. washthe residue is washed with trichloroethylene
  5. customrecrystallised from 200 ml of water
  6. customThe crystals which have precipitated
  7. filtrationare filtered off
  8. stirringstirred for one hour at 75°C
  9. customseparated from the organic solvent by filtration
  10. customdried at 80°C

Quellen und Nachweise

ORD-Eintrag
ord-be9aab24b5504072bd01e51661a3a3ab
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03957860

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