Dimethyl Sulfate → HCID 601943, Verbindung

HRID 508767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508767
[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-1a395de7403f43f28256c444554cafc0
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

Notizen zur Reaktion

Wird geladen…