Sodium hydride → HCID 86648969, Verbindung

HRID 449936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449936
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[H-].[Na+].[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:13]=1[C:14](Cl)=[O:15].CCOCC.CCCCCC>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:14](=[O:15])[C:13]2[C:12]([Cl:11])=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:21])[CH:3]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 783922,6-Dichlorobenzoyl chlorideHCID 2380124-Amino-6-chloropyrimidineHCID 21584099Diethylether hexane

Produkt 1

HCID 86648969HCID 86648969, VerbindungAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled (0° C.) solution of 6-chloropyrimidin-4-amine (1.295 g, 10 mmol) in DMF (25 mL) was added sodium hydride (1.2 g, 30 mmol, 60% dispersion in mineral oil) in one portion. The mixture was stirred at 0° C. for 10 min and then 2,6-dichlorobenzoyl chloride (2.304 g, 11 mmol) was added dropwise. The mixture was warmed to room temperature and stirred under nitrogen overnight. The mixture was quenched with ice water and the resulting precipitate was collected by filtration. The solid was washed with water, then 1:1 ether/hexane (10 mL,) to give N-(6-chloropyrimidin-4-yl)-2,6-dichlorobenzamide (1.95 g, yield: 64%). 1H NMR (500 MHz, DMSO) δ 12.09 (s, 1H), 8.84 (s, 1H), 8.24 (s, 1H), 7.61-7.56 (m, 2H), 7.53 (dd, J=9.2, 6.8 Hz, 1H). LCMS (ESI) m/z: 302.1 [M+H+].

Aufarbeitung

  1. temperatureThe mixture was warmed to room temperature
  2. stirringstirred under nitrogen overnight
  3. customThe mixture was quenched with ice water
  4. filtrationthe resulting precipitate was collected by filtration
  5. washThe solid was washed with water

Quellen und Nachweise

ORD-Eintrag
ord-05bf36efbaea41deb25c5c872508cf25
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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