Formic Acid → {4-[(E)-3-(3-Chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde

HRID 1867357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867357
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH:21](OCC)[O:22]CC)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1.C(O)=O.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH:21]=[O:22])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 962WaterHCID 684321531-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(2,2-diethoxy-ethyl)-[1,4]diazepan-5-one

Produkt 1

HCID 86615865{4-[(E)-3-(3-Chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehydeAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1.00 g (2.53 mmol) of 1-[(E)-3-(3-chloro-phenyl)-acryloyl]-4-(2,2-diethoxy-ethyl)-[1,4]diazepan-5-one in 10 ml of toluene was treated at RT with 5.22 ml formic acid and 1.5 ml water. The reaction was stirred for 1.5 h, evaporated and neutralized with aqueous saturated NaHCO3 and extracted with Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (EtOAc) to yield 0.37 g (45%) of the title compound as off-white foam. MS: 321.3 (MH+, Cl).

Aufarbeitung

  1. customevaporated
  2. extractionextracted with Et2O (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by flash silica gel column (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4c256c09299f4815929677b541b84b1c
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632829B2

Notizen zur Reaktion

Wird geladen…