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

HRID 1183668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1183668
[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. The reaction mixture was diluted with water and extracted with DCM (2×50 mL). The combined organic layers were dried over Na2SO4, filtered and the volatiles removed in vacuo. The crude reaction mixture was purified by column chromatography to give ethyl 2-(4-amino-3-chloro-5-(cyclopropylmethoxy)phenyl)acetate (920 mg) as a yellow solid.

Aufarbeitung

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe volatiles removed in vacuo
  5. customThe crude reaction mixture
  6. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ddaef55093594b5baef8f51ed80cfedd
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664249B2

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