Chlorosuccinimide → Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate

HRID 1512523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512523
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[O:14][CH2:15][CH:16]1[CH2:18][CH2:17]1.C1C(=O)N([Cl:26])C(=O)C1>C(Cl)(Cl)(Cl)Cl.O>[NH2:1][C:2]1[C:3]([O:14][CH2:15][CH:16]2[CH2:18][CH2:17]2)=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][C:7]=1[Cl:26]

Komponenten

5

Edukt 2

HCID 31398ChlorosuccinimideHCID 57995628Ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate

Produkt 1

HCID 57995503Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetateAusbeute 101,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 2-(4-amino-3-(cyclopropylmethoxy)phenyl)acetate (1.2 g, 4.0 mmol) in dry CCl4 (60 mL), NCS (0.427 g, 3.2 mmol) was added at 0° C. The reaction mixture was allowed to stir for 3 h at room temperature to complete the reaction. The reaction mixture was diluted with water, extracted with DCM (2×50 mL), the combined organic solvents was dried over Na2SO4, filtered and concentrated in vacuo. The crude reaction mixture was purified by column chromatography to yield Ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate (920 mg) as a yellow solid.

Aufarbeitung

  1. customthe reaction
  2. extractionextracted with DCM (2×50 mL)
  3. dry with materialthe combined organic solvents was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude reaction mixture
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4900d88c5ffb44ac958771e9fb0a52db
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217064B2

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