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Acetonitrile → methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate

HRID 1807840
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1807840
F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=1.FC1C=CC(C(OC)=O)=C(C)C=1[N+]([O-])=O.[CH:31]1([C:36]2[NH:37][CH:38]=[CH:39][N:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1.C(#N)C>C(OCC)(=O)C.O.C(N(CC)CC)C>[CH:31]1([C:36]2[N:37]([C:2]3[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:15])[CH:3]=3)[CH:38]=[CH:39][N:40]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1
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Komponenten

8

Edukt 4

HCID 6342AcetonitrileHCID 150886132-Cyclopentyl-1H-imidazoleHCID 51342041Methyl 4-fluoro-2-methyl-5-nitrobenzoateHCID 58575232Methyl 4-fluoro-2-methyl-3-nitrobenzoate

Produkt 1

HCID 58575136methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 8471TriethylamineLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 2.74 g of a mixture of methyl 4-fluoro-2-methyl-5-nitrobenzoate and methyl 4-fluoro-2-methyl-3-nitrobenzoate, 1.75 g of 2-cyclopentyl-1H-imidazole, and 17.5 mL of acetonitrile, was added 4.9 mL of triethylamine, followed by stirring at 70° C. for 7 hours. To the reaction mixture were added water and ethyl acetate, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and then solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 2.12 g of methyl 4-(2-cyclopentyl-1H-imidazol-1-yl)-2-methyl-5-nitrobenzoate.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customsolvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-80db762bcda749ac84aaaf5365c39d6a
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08357688B2

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