N,N-Dimethylaniline → N-(4-Amino-3-nitro-phenyl)-4-isopropyl-benzenesulfonamide

HRID 450723

Reaktionsgleichung

Reaktionsgleichung von HRID 450723
[N+:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH2:11])([O-:3])=[O:2].CN(C)C1C=CC=CC=1.[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([CH3:23])[CH3:22]>C(#N)C>[NH2:11][C:5]1[CH:6]=[CH:7][C:8]([NH:10][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH:21]([CH3:23])[CH3:22])=[CH:25][CH:26]=2)(=[O:32])=[O:31])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 949N,N-DimethylanilineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 43383702-Nitro-4-phenylenediamine

Produkt 1

HCID 27993411N-(4-Amino-3-nitro-phenyl)-4-isopropyl-benzenesulfonamideAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 2-nitro-benzene-1,4-diamine (10 g, 65.30 mmol) and N,N-dimethylaniline (8.7 g, 71.83 mmol) in acetonitrile (310 ml) at 0° C. 4-isopropyl-benzenesulfonylchloride (13.85 g, 63.34 mmol) was added over a period of 1 h. The mixture was stirred at 0° C. for 1 h and for 16 h at room temperature. After concentrating the mixture in vacuo the obtained oil was triturated with water. The precipitate was collected, washed with ethanol and dried in vacuo to give the product as a yellow powder (11.76 g, 54%).

Aufarbeitung

  1. concentrationAfter concentrating the mixture in vacuo the obtained oil
  2. customwas triturated with water
  3. customThe precipitate was collected
  4. washwashed with ethanol
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d1517fabb6114385b7dc8398287ec5a8
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486984B2

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