Dimethylamine → HCID 59442004, Verbindung

HRID 1014386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1014386
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20](Cl)=[O:21].[CH3:23][NH:24][CH3:25]>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH3:11])[C:20](=[O:21])[CH2:19][N:24]([CH3:25])[CH3:23]

Komponenten

7

Edukt 4

HCID 674Dimethylamine2×HCID 11430Potassium CarbonateHCID 89602Bromoacetyl chlorideHCID 145678141208091-01-3

Produkt 1

HCID 59442004HCID 59442004, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of N,2-dimethyl-4-(methyloxy)aniline (5.10 g, 33.7 mmol) and potassium carbonate (9.32 g, 67.5 mmol) in tetrahydrofuran (150 ml) was treated with bromoacetylchloride (3.50 ml, 42.2 mmol), stirred for 45 minutes, and dimethyl amine in tetrahydrofuran (67.5 ml, 135 mmol) was added. The solution was stirred for 3 hours, additional dimethyl amine in tetrahydrofuran (67.5 ml, 135 mmol) was added, and the solution was warmed to 50° C. and maintained overnight. The solution was cooled, poured into ethyl acetate/saturated sodium bicarbonate, and the organic layer was separated, dried over sodium sulfate, filtered, taken to a residue under reduced pressure, and purified by column chromatography to afford N1,N2,N2-trimethyl-N1-[2-methyl-4-(methyloxy)phenyl]glycinamide (5.10 g, 21.58 mmol, 64.0% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6); two protons likely obstructed by DMSO; δ ppm 7.13 (d, J=8.6 Hz, 1 H), 6.90 (d, J=2.6 Hz, 1 H), 6.77-6.84 (m, 1 H), 3.76 (s, 3 H), 3.00 (s, 3 H), 2.13 (s, 3 H), 2.08 (s, 6 H).

Aufarbeitung

  1. stirringThe solution was stirred for 3 hours
  2. temperaturemaintained overnight
  3. temperatureThe solution was cooled
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5429ec0cd98242bc9498e5b1bfe348de
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981903B2

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