Dimethyl Sulfate → HCID 601943, Verbindung

HRID 59278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59278
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[OH-].[Na+].S(OC)(O[CH3:19])(=O)=O>C1(C)C=CC=CC=1>[CH3:19][NH:6][C:5]1[CH:7]=[C:8]([CH3:9])[C:2]([CH3:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 814454,5-Dimethyl-2-nitrobenzenamine

Produkt 1

HCID 601943HCID 601943, VerbindungAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 4,5-dimethyl-2-nitroaniline (2.00 g, 12 mmol) in toluene (25 mL) was added NaOH (1.93 g, 48 mmol). The reaction mass was stirred at 100° C. for 1 h, followed by addition of dimethyl sulphate (4.6 g, 36 mmol) and reaction mass was stirred at RT for 24 h. The reaction mass was quenched in water, extracted with DCM and concentrated to afford 1.5 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 2.11 (s, 3H), 2.24 (d, J=7.8 Hz, 3H), 2.92 (s, 3H), 6.77 (m, 1H), 7.79 (m, 1H), 8.06 (s, 1H); MS (m/z): 180.92 (M+H)+.

Aufarbeitung

  1. stirringwas stirred at RT for 24 h
  2. customThe reaction mass was quenched in water
  3. extractionextracted with DCM
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b1757f46b4746dca18661e058db2ef1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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