Triethylamine → 3-(2-fluoro-phenyl)-N-methoxy-N-methyl-acrylamide

HRID 857008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857008
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](O)=[O:7].CCN=C=NCCC[N:21]([CH3:23])C.Cl.C(N(CC)CC)C.N[O:33][CH3:34].Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([N:21]([O:33][CH3:34])[CH3:23])=[O:7]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 738515733-(2-fluoro-phenyl)-N-methoxy-N-methyl-acrylamideAusbeute 95,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-fluorocinnamic acid (16.6 g), EDAC.HCl (23 g), DMAP (12.2 g), triethylamine (28 mL), and NH2OMe.HCl (12 g) in CH2Cl2 (300 mL) was stirred at room temperature for 16 h. The reaction was quenched with water, and the organic layer was washed with brine, dried over MgSO4 and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by silica gel flash chromatography eluting with 33% hexanes in ethyl acetate gave the title compound (20 g) as a solid.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrated was evaporated in vacuo
  6. customthe crude product was purified by silica gel flash chromatography
  7. washeluting with 33% hexanes in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8f925e2269cb4d159f3efe54ff03600a
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144881B2

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