1,3-Dimethylimidazolium Iodide → (2-Chloro-5-methyl-4-pyrimidinyl)[3-(trifluoromethyl)phenyl]methanone

HRID 1060526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060526
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][N:3]=1.[F:10][C:11]([F:21])([F:20])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16].[I-].C[N+]1C=CN(C)C=1.[H-].[Na+]>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([C:15]([C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([C:11]([F:10])([F:20])[F:21])[CH:13]=2)=[O:16])[C:5]([CH3:9])=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 203341,3-Dimethylimidazolium IodideHCID 24758Sodium hydrideHCID 679903-(Trifluoromethyl)benzaldehydeHCID 74508Pyrimidine, 2,4-dichloro-5-methyl-

Produkt 1

HCID 18628524(2-Chloro-5-methyl-4-pyrimidinyl)[3-(trifluoromethyl)phenyl]methanoneAusbeute 32,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2,4-Dichloro-5-methylpyrimidine (3.6 g, 18.4 mmol) was dissolved in dichloromethane (50 mL) and treated sequentially with 3-trifluoromethylbenzaldehyde (3.3 g, 18.4 mmol), and 1,3-dimethylimidazolium iodide (1.37 g, 6.2 mmol). Sodium hydride (0.74 g, 18.4 mmol) was added and an exotherm was noted. After being heated at reflux for 3 h, the reaction was quenched with water and the layers were separated. The dried (magnesium sulfate) organic layer was purified by chromatography on silica gel using hexanes/ethyl acetate 85:15 as eluent. The title compound of Step A (1.8 g) was isolated as a white solid melting at 113-116° C. 1H NMR (CDCl3/200 MHz) 2.39 (s, 3H), 7.66 (m, 1H), 7.90 (d, 1H), 8.07 (s,1H), 8.69 (s, 1H).

Aufarbeitung

  1. temperatureAfter being heated
  2. temperatureat reflux for 3 h
  3. customthe reaction was quenched with water
  4. customthe layers were separated
  5. dry with materialThe dried (magnesium sulfate) organic layer
  6. customwas purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f1b6b4f6366d4311959286abaa6d3c20
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06525001B1

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