Acryloyl chloride → [4-(Acryloylmethylamino)phenyl]acetic Acid Methyl Ester

HRID 2412300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2412300
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:13][O:12][C:10](=[O:11])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([NH:2][CH2:1][C:23](=[O:26])[CH:24]=[CH2:25])=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 15892780Methyl 2-(4-(methylamino)phenyl)acetate

Produkt 1

HCID 66770363[4-(Acryloylmethylamino)phenyl]acetic Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl (4-methylaminophenyl)acetate (4.00 g, 22.3 mmol) and N,N-diisopropylethylamine (7.78 mL, 44.6 mmol) in DCM (20.0 mL) at 0° C. was slowly added 2-propenoyl chloride (2.18 mL, 26.8 mmol). The reaction mixture was stirred at room temperature for 2 h and then saturated aqueous sodium bicarbonate (20.0 mL) was added. This mixture was extracted with DCM (10 mL) and the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used in the next reaction without further purification.

Aufarbeitung

  1. customat 0° C.
  2. extractionThis mixture was extracted with DCM (10 mL)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b1e2c825401e4b438f577f7e08bdff85
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816088B2

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