Acetic Acid → 4-[[(4-Nitrophenyl)sulfonyl]amino]-3-methylphenol

HRID 27656

Reaktionsgleichung

Reaktionsgleichung von HRID 27656
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11].O.C(O)(=O)C>N1C=CC=CC=1>[N+:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])(=[O:21])=[O:20])=[CH:17][CH:18]=1)([O-:12])=[O:11]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 178194-Amino-m-cresol

Produkt 1

HCID 233416514-[[(4-Nitrophenyl)sulfonyl]amino]-3-methylphenolAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred mixture of 4-amino-3-methylphenol (24 g, 0.2 mole) in 600 ml of pyridine was added all at once p-nitrobenzenesulfonyl chloride (Eastman) (45 g, 0.2 mole) followed by heating on a steam bath for 2 hours. The dark oily solution was poured into 4 liters of water and then treated with glacial acetic acid until acid. The tar crystallized on standing to give after filtration 67 g (100%) of brown solid. The entire sample was recrystallized from CH3NO2 to give 52 g of pure intermediate.

Aufarbeitung

  1. temperatureby heating on a steam bath for 2 hours
  2. customThe tar crystallized
  3. customto give
  4. filtrationafter filtration 67 g (100%) of brown solid
  5. customThe entire sample was recrystallized from CH3NO2

Quellen und Nachweise

ORD-Eintrag
ord-6f7d5deaa49f4f3980efc0c7edca883c
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04222948

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