Methyl bromoacetate → HCID 13280936, Verbindung

HRID 1903632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903632
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:7](=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33]>CN(C)C=O.O>[CH3:35][O:34][C:32](=[O:33])[CH2:31][N:19]1[C:20]([CH3:21])=[C:6]2[C:7]([CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:23]=[CH:22][C:5]=32)=[CH:18]1

Komponenten

6

Edukt 3

HCID 60984Methyl bromoacetateHCID 13067111HCID 13067111, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 13280936HCID 13280936, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In one portion, 2.0 g (5.8 mmol) of 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine were added to an ice-cooled solution of 0.8 g (7.1 mmol) of potassium t-butoxide in 30 ml of dry dimethylformamide. After stirring at 0° C. for 15 minutes, 0.65 ml (7.7 mmol) of methyl bromoacetate was added, and the resulting solution was stirred for 5 minutes. The mixture was diluted with water and extracted with ether. The ether solution was washed with water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to an oily residue. Purification of the residue by column chromatography (silica gel, 40 g; eluent, 5% ether in methylene chloride) gave after crystallization from a mixture of ether and petroleum ether 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid methyl ester as off-white prisms, mp 174°-176° C.

Aufarbeitung

  1. stirringthe resulting solution was stirred for 5 minutes
  2. extractionextracted with ether
  3. washThe ether solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure to an oily residue
  6. customPurification of the residue by column chromatography (silica gel, 40 g; eluent, 5% ether in methylene chloride)
  7. customgave
  8. customafter crystallization
  9. additionfrom a mixture of ether and petroleum ether 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine-2-acetic acid methyl ester as off-white prisms, mp 174°-176° C.

Quellen und Nachweise

ORD-Eintrag
ord-d7d8195b7f364789a0f6f62dfec0f105
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436662

Notizen zur Reaktion

Wird geladen…