o-Toluenesulfonyl chloride, 5-nitro- → 2-Methyl-5-nitrobenzene-1-sulfonamide

HRID 277584

Reaktionsgleichung

Reaktionsgleichung von HRID 277584
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[OH-].[NH4+:16]>C(OCC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([NH2:16])(=[O:13])=[O:12]

Komponenten

4

Edukt 2

HCID 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 14923Ammonium Hydroxide

Produkt 1

HCID 2342822-Methyl-5-nitrobenzene-1-sulfonamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a round bottom flask under nitrogen was placed commercially available 2-methyl-5-nitrobenzene sulphonyl chloride (2.36 g, 10.0 mmol) and 75 L dry ethyl ether was added. The solution was cooled to 0° C. and concentrated ammonium hydroxide (10 mL) was added. After stirring overnight, the mixture was filtered and then diluted with dichloromethane (150 mL). The organic layer was separated and dried over MgSO4. The solution was then concentrated to afford 820 mg of the title compound as a white solid (38%): 1HNMR (DMSO-d6) δ8.61 (d, J=2.5 Hz, 1H), 8.35 (dd, J=8 Hz, 2.5 Hz, 1H), 7.79 (br s, 2H), 7.70 (d, J=8 Hz, 1H), 2.71 (s, 3H).

Aufarbeitung

  1. customIn a round bottom flask under nitrogen was placed commercially available
  2. filtrationthe mixture was filtered
  3. additiondiluted with dichloromethane (150 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationThe solution was then concentrated

Quellen und Nachweise

ORD-Eintrag
ord-67f09f193ae047fe86dd166c0ea4709f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355633B1

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