Sodium Carbonate → HCID 57864336, Verbindung

HRID 1672612

Reaktionsgleichung

Reaktionsgleichung von HRID 1672612
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][NH:16][CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.Br[CH2:31][CH2:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][N:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=2)[CH2:31][CH2:32][C:33]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=2)=[CH:28][CH:29]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 128865484-(2-Bromoethyl)benzonitrile2×HCID 22014995Methyl 4-({2-[2-(4-bromobenzyloxy)phenyl]ethylamino}methyl)benzoate

Produkt 1

HCID 57864336HCID 57864336, VerbindungAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

200 mg (0.44 mmol) of methyl 4-({2-[2-(4-bromobenzyloxy)phenyl]ethylamino}methyl)benzoate from Example 5A, 101 mg (0.48 mmol) of 4-(2-bromoethyl)benzonitrile and 51.4 mg (0.48 mmol) of sodium carbonate are heated in 5 ml of acetonitrile to reflux for 5 hours. A further 101 mg (0.48 mmol) of 4-(2-bromoethyl)benzonitrile are then added, and the reaction solution is stirred further under reflux overnight. After the reaction solution has cooled, the mixture is concentrated to dryness, and the residue is taken up in ethyl acetate and washed with water and saturated sodium chloride solution. Drying over sodium sulfate is followed by filtration and concentration. The crude product is purified by preparative HPLC. 183 mg (0.31 mmol, 69% yield) of a pale yellow oil are obtained.

Aufarbeitung

  1. temperatureto reflux for 5 hours
  2. temperatureunder reflux overnight
  3. temperatureAfter the reaction solution has cooled
  4. concentrationthe mixture is concentrated to dryness
  5. washwashed with water and saturated sodium chloride solution
  6. dry with materialDrying over sodium sulfate
  7. filtrationis followed by filtration and concentration
  8. customThe crude product is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1f957519f4314044a0714ae332694a96
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998988B2

Verknüpfte Notizen

Wird geladen…