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

HRID 1512456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512456
[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-bf39278f75fd44dfbfe4d80518368afc
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217064B2

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