1-Methylimidazole → (2-amino-5-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methanone

HRID 730101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730101
[Li]CCCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[NH2:12][C:13]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:14]=1[C:15](O)=[O:16].[NH4+].[Cl-]>CCCCCC.CCOCC>[NH2:12][C:13]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:14]=1[C:15]([C:8]1[N:7]([CH3:6])[CH:11]=[CH:10][N:9]=1)=[O:16]

Komponenten

7

Edukt 4

HCID 13901-MethylimidazoleHCID 124762-Amino-5-chlorobenzoic acidHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 10998977(2-amino-5-chlorophenyl)(1-methyl-1H-imidazol-2-yl)methanoneAusbeute 13,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of nBuLi (0.0730 mol) in hexane was added N-methyl imidazole (0.0608 mol) drop wise at −40° C. over 30 min under a nitrogen atmosphere. The resulting yellow solution was stirred for a further 3 hr at rt, and then refluxed for 1 h. 2-amino-5-chlorobenzoic acid (1.74 g, 0.01014 mole) in dry ether (60 ml) was then added to the reaction mixture. The reaction mixture was stirred overnight at rt. To the reaction mixture was added saturated NH4Cl solution and the resulting mixture extracted with ethyl acetate (2×150 ml). The combined organic layers were dried over Na2SO4. After removal of solvent, the residue was purified by the flash chromatography using ethyl acetate/hexane (1:4) as eluent. Crystallization of the product from Et2O/hexane mixture gave 300 mg (13.7%) of product as yellow solid.

Aufarbeitung

  1. temperaturerefluxed for 1 h
  2. stirringThe reaction mixture was stirred overnight at rt
  3. extractionthe resulting mixture extracted with ethyl acetate (2×150 ml)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customAfter removal of solvent
  6. customthe residue was purified by the flash chromatography
  7. customCrystallization of the product from Et2O/hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-c4fe80a84182482eb6dfdcf0dcb3cc17
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582661B2

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